1-Butanol → {4-[(2-Amino-6-chloropyrimidin-4-yl)amino]cyclopent-2-en-1-yl}methanol

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Reaction Steps

To 14 mmol of crude 2a, 2-amino-4,6-dichloropyrimidine (3.74 g, 22.8 mmol), triethylamine (15 ml) and n-butanol (75 ml) were added and the mixture was refluxed for 48 hr. The volatile solvents were removed, residue was treated with methanol to separate the undissolved byproduct (the double pyrimidine nucleoside). The methanol solution was absorbed on silica gel (8 g) packed into a column (4.0×14 cm) and eluted with CHCl-MeOH (40:1) to yield 1.52 g (42%) of crude 4a. The product was recrystalized from ethyl acetate to yield 4a; mp 132-134° C., MS (30 ev, 200° C.); m/e 240 and 242 (M+ and M++2), 209 (M+−31), 144 (B+); IR: 3600-3000 (NH2, OH), 1620,1580 (C═C, C═N); Anal. (C10H13ClN4O) C,H,N.

Provenance & Evidence