ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Spontaneous Opening of the Pyrimidine Ring of Pyrrolo[2,3-d]pyrimidines after Intramolecular AcylationPhase-transfer alkylation of 4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine (2) with ethyl 3-bromopropionate leads regioselectively to the ester 3a. After displacement of its methylthio group and saponification of the ester function, the acid 3e is obtained which can be transferred to the functionalized deazahypoxanthine 3f by either treatment with dry HBr/glacial AcOH or by nucleophilic displacement of the 4-methoxide. Reaction of 3f with a H2O-soluble carbodiimide results in an intramolecular acylation at N(1) by the activated ester; the intermediate 4 undergoes spontaneous hydroxylation and subsequent opening of the pyrimidine ring under formation of the pyrrolo[1,2-a]pyrimidine derivative 6. Its structure was proved by X-ray analysis. Subsequent deformylation of 6 in alkaline medium leads to the compound 7 in almost quantitative yield.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680226
