Patent ID: 6448402
Filing Date: 2002-09-10
Classification: C07B,C07C,C07D,C12P

Abstract:
A process for the preparation of (1S,4R)-4-(2-amino-6-chloro-9H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formula or the mirror image thereof comprising the steps of:(A) reducing (1R,4S)-2-azabicyclo[2.2.1 ]hept-5-en-3-one of the formula â€ƒor the mirror image thereof with lithium borohydride to yield (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene of the formula â€ƒor the mirror image thereof; (B) converting the (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene or mirror image thereof to a hydrohalide salt thereof; (C) reacting the hydrohalide salt formed in step (B) with N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide of the formula â€ƒto yield (1S,4R)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl- 1-methanol of the formula â€ƒor the mirror image thereof; and (D) cyclizing the (1S,4R)-4-[(2-amino-6-chloro-formamido-4-pyrimidinyl)-amino]-2-cyclopentenyl-1-methanol or the mirror image thereof to yield (1S,4R)-4-(2-amino-6-chloro-9H-purine-9-yl)-2-cyclopentenyl-1-methanol or the mirror image thereof.