US EPA

7443540 

Journal Article 

SYNTHESIS OF METHYL 9-BENZYLGUANINE-8-CARBAMATE - A CONVENIENT SYNTHESIS OF OXAZOLO[5,4-D]PYRIMIDINES AND THEIR CONVERSION INTO IMIDAZO[4,5-D]PYRIMIDINES VIA A CARBODIIMIDE-MEDIATED REARRANGEMENT 

Chern, JW; Lee, HY; Wise, DS; Townsend, LB 

1988 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

53 

24 

5617-5622 

English 

10.1021/jo00259a004 

WOS:A1988R227700004 

The reaction of 2,5-diamino-4-(benzylamino)pyrimidin-6(lH)-one (5) with N-(methoxycarbonyi)-S-methylpseudothiourea furnished 2-amino-4-(benzylamino)-5-[1-[3-(methoxycarbonyl)guanidino]]pyrimidin-6(1H)-one (6). Although compound 6 should be a precursor for the synthesis of the title compound 4, the cyclization of compound 6 could not be effected by using standard conditions. Cyclodesulfurization of 2-amino-4-(benzylamino)-5-[1-[3-(methoxycarbonyl)thioureido]]pyrimidin-6(1H)-one (7), with dicyclohexylcarbodiimide in N,Ndimethylformamide, furnished methyl 6-amino-4-(benzylamino)oxazolo[5,4-d]pyrimidine-2-carbamate (9) in 88% yield. The title compound 4 was synthesized via a thermal or base-catalyzed rearrangement of compound 9, or from 2-amino-4-(benzylamino)-5-[1-[3-(methoxycarbonyl)-S-methylpseudothioureido]]pyrimidin-6(1/f)-one (8) by using base catalysis. © 1988, American Chemical Society. All rights reserved. 

9 benzyl 8 guaninecarbamic acid methyl ester; imidazo[4,5 d]pyrimidine derivative; oxazolo[5,4 d]pyrimidine derivative; unclassified drug; drug synthesis; infrared spectrophotometry; nonhuman; nuclear magnetic resonance; ultraviolet spectrophotometry