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    References - Sir

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    References - Sir

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    Rupalikiran
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    References - Sir

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    of 4

    CAS NO: 56-06-4

    CAS NAME: 4(3H)-Pyrimidinone, 2,6-diamino-

    STRUCTURE:
    NH2

    N NH

    O NH2

    SYNTHESIS REFERENCES:
    DFT simulations and vibrational analysis of FT-IR and FT-Raman spectra of
    2,4-diamino-6-hydroxypyrimidine. Subramanian, M. K.; Anbarasan, P. M.;
    Manimegalai, S. Department of Physics, Thiruvalluvar Govt. Arts College,
    Rasipuram, Namakkal, Tamilnadu, India. Spectrochimica Acta, Part A: Molecular and
    Biomolecular Spectroscopy (2009), 73A(4), 642-649. Publisher: Elsevier B.V.,
    Abstract - Quantum mech. calcns. of energies, geometries and vibrational
    wavenumbers of 2,4-diamino-6-hydroxypyrimidine (2,4DA6HP) were carried out by
    using ab initio HF and d. functional theory (DFT/B3LYP) method using 6-311G(d,p)
    basis set. The optimized geometrical parameters obtained by B3LYP method show
    good agreement with exptl. X-ray data. The best level of theory in order to
    reproduce the exptl. wavenumbers is B3LYP method with the 6-311G(d,p) basis set.
    The difference between the obsd. and scaled wavenumber values of most of the
    fundamentals is very small. A detailed interpretation of the IR spectra of 2,4DA6HP
    was also reported. The calcd. HOMO and LUMO energies show that charge transfer
    occurs in the mol. The entropy of the title compd. is also performed at HF/6-
    311G(d,p) and B3LYP/6-311G(d,p) levels of theory. The theor. spectrograms for FT-
    IR and FT-Raman spectra of the title mol. have been constructed.

    2,4-Diamino-6-hydroxypyrimidine. VanAllan, J. A. Eastman Kodak


    Company, Rochester, NY, USA. Organic Syntheses (1952), 32 No pp. given.
    Publisher: John Wiley & Sons, Inc.
    Abstract - A review of the article 2,4-Diamino-6-hydroxypyrimidine.

    RO104937 - Preparation of 2,4-diamino-6-hydroxypyrimidine via the


    cyclocondensation of ethyl cyanoacetate with guanidinium nitrate.
    Vasilioni, Virgil Gheorghe; Darabantu, Mircea; Fodor, Cristina; Serban, Gabriel;
    Balint, Radu Dorin; Breazu, Dorin. (Intreprinderea de Medicamente "Terapia",
    Rom.). Rom. (1994), 3 pp.
    Abstract - 2,4-Diamino-6-hydroxypyrimidine is prepd. in high yield and purity by
    dissolving guanidinium nitrate in methanolic or ethanolic NaOH (the molar ratio of
    NaOH-alc. is 1:3.8) at 40, adding (at 70-72; the molar ratio of Et cyanoacetate-
    guanidinium nitrate is 1:1.1), removing the alc. solvent, dissolving the intermediate
    Na salt of 2,4-diamino-6-hydroxypyrimidine in H2O, neutralizing this aq. soln. with
    37% aq. HCl, cooling the product-contg. soln. to 2, and filtering the 2,4-diamino-
    6-hydroxypyrimidine.

    EP304648 - Preparation of 2,4-diamino-6-piperidinopyrimidine 3-oxide


    (minoxidil) and intermediates therefor. Maignan, Jean; Restle, Serge; Lang,
    Gerard. (Oreal S. A., Fr.). Eur. Pat. Appl. (1989), 17 pp.
    Abstract -The title compd. (I), a known antihypertensive, was prepd. from
    pyrimidine derivs. II (X = halo, OH) and/or pyrimidine oxides III (X = OH, Cl, o-
    tosyl, O-benzenesulfonyl; R1,R2 = H, RNHCO; R = C1-6 alkyl; one of R1 = R2 must
    be other than H; n = 0 or 1). Reaction of 6-chloro-2,4-diaminopyrimidine with
    BuNCO, followed by oxidn. with m-chloroperbenzoic acid, reaction with piperidine,
    and deprotection by treatment with KOH, gave I.

    X
    X

    N
    N

    R 1HN N NHR 2
    H2N N NH 2 II On III

    EP295218 - Process for the preparation of minoxidil via a pyrimidine N-


    oxide. Botre, Claudio. (Italy). Eur. Pat. Appl. (1988), 6 pp.
    Abstract - Minoxidil (I) is prepd. as an antihypertensive. Cyclocondensation of
    H2NC(:NH)NH2.HCl with NCCHCO2Et in EtOH in the presence of MeONa gave 79.6%
    2,6-diamino-4-hydroxypyrimidine, which was treated with POCl3 to afford 47.3% II
    (n = 0). Treatment of the pyrimidine in MeOH with III gave 66.9% II (n = 1), which
    was treated with an excess to piperidine to yield 75.9% I.
    Cl N NH 2
    CO 3 H
    NO n Mg 2+ ⋅ 6H 2 O

    CO 2 -
    NH 2 II 2 III

    HU19770 - 6-Piperidino-2,4-diaminopyrimidine 3-oxide. Szentay, Csaba;


    Balogh, Gyula; Horvath, Judit; Master, Tamas. (E. Gy. T. Gyogyszervegyeszeti Gyar,
    Hung.). Hung. Teljes (1981), 18 pp.
    Abstract - The title compd. (I) is prepd. from 6-hydroxy-2,4-diaminopyrimidine (II)
    by sulfonylation with RSO2Cl (R = Ph, p-tolyl, Me), oxidn. with m-ClC6H4CO2OH
    (III), and treatment with piperidine (IV). Thus, a soln. of II in 2.5 N NaOH and p-
    MeC6H4SO2Cl in Me2CO were added simultaneously to Me2CO at room temp. and
    pH 7, and the mixt. was stirred 3 h to give 95% 6-(p-tolylsulfonyloxy)-2,4-
    diaminopyrimidine. Oxidn. of the latter with III in aq. EtOH at 0-5 gave 65% 6-(p-
    tolylsulfonyloxy)-2,4-diaminopyrimidine 3-oxide, which on heating with piperidine 2
    h at 100 gave 55% I.

    GB2032434 - 6-Piperidino-2,4-diaminopyrimidine-3-oxide. Vedres, Andras;


    Szantay, Csaba; Balogh, Gyula; Horvath, Judit; Mester, Tamas. (E. Gy. T.
    Gyogyszervegyeszeti Gyar, Hung.). Ger. Offen. (1980), 33 pp.
    Abstract - The title compd. (I), a known antihypertensive, was prepd. from 2,4-
    diamino-6-pyrimidinol (II). Thus, II was O-tosylated with 4-MeC6H4SO2Cl, and the
    product was treated with 3-ClC6H4CO3H to give III, which was treated with
    piperidine at 0-5, followed by heating 3 h at 100 to give 64% I.

    NH 2 Cl

    Me SO 3 N O2 C
    N
    NH III

    Vibrational spectra of biological molecules: 2,4-diamino-6-


    hydroxypyrimidine. Goel, R. K.; Sharma, S. N. Dep. Phys., D. N. Coll.,
    Meerut, India. Indian Journal of Pure and Applied Physics (1980), 18(3), 195-9.
    CODEN: IJOPAU ISSN: 0019-5596. Journal written in English. CAN 92:210384
    AN 1980:210384 CAPLUS (Copyright (C) 2010 ACS on SciFinder (R))
    Abstract - The IR absorption spectra of 2,4-diamino-6-hydroxypyrimidine were
    recorded on the Perkin Elmer-521 spectrophotometer in the region 250-4000 cm-1
    by KBr pellet and Nujol mull techniques. The spectra were analyzed assuming C8
    point-group symmetry for the mol. The fundamentals were compared with those of
    pyrimidine. Assignments were proposed and discussed. Tautomerism is also
    discussed.

    SU517591 - N6-Substituted 2,6-diamino-4-hydroxypyrimidines. Zav'yalov,


    S. I.; Ovechkina, L. F.; Pokhvisneva, G. V. (Zelinskii, N. D., Institute of Organic
    Chemistry, USSR). U.S.S.R. (1976),
    Abstract - The title compds. I (R1 = CH2CH2OH, cyclohexyl, Bu) were prepd. by
    transamination of I with the corresponding R1NH2 in HOCH2CH2CH2OH contg.
    Cu(OAc)2 at 170-200 .

    HO

    N
    I, R=R 1
    H2 N N NHR II, R=H

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