2-amino-3,5-di-(halomethyl)-pyrazines and their preparation

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

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544336, C07D40304, C07D24120

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046925279

ABSTRACT:
2-Amino-3,5-di-(halomethyl)-pyrazines of the general formula I ##STR1## where X is either chlorine or bromine, m and n may each be 0, 1, 2 or 3 and R.sup.1 and R.sup.2 are each hydrogen or a protective group or may furthermore be bonded to one another, in particular those compounds of the formula I in which m is 1 and n is 2 and/or R.sup.1 and R.sup.2 together form a phthaloyl radical, are useful intermediates for the pteridine building block of folic acid or folic acid analogs.
They are obtained by a method in which a 2-amino-3,5-dimethylpyrazine of the general formula II ##STR2## is treated with a chlorinating or brominating agent and, where R.sup.1 and/or R.sup.2 are protective groups, these are, if desired, eliminated when the chlorination or bromination is complete.

REFERENCES:
patent: 3320126 (1967-05-01), Meltzer
Hirschberg, et al., J. Organic Chem., vol. 26, (1961) pp. 2356-2360.
Sharp, et al., Chem. Abstracts, vol. 46, (1952), entry 2083h.
E. C. Taylor et al., J. Org. Chem. vol. 43, No. 4, 1978, p. 736.
E. C. Taylor et al., J. Org. Chem. 45, 1980, pp. 2485 to 2489.
E. C. Taylor et al., J. Org. Chem. 46, 1981, pp. 1394 to 1402.
Houben-Weyl, Methoden der Org. Chemie, vol. 5/3, Georg-Thieme Verlag Stuttgart, 1962, pp. 728, 731, 748.

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