Ammonia → 7-Amino-1-[(1,3-dihydroxy-2-propoxy)methyl]-1, 3-azaphospholo [4,5-d]pyrimidine

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Reaction Steps

A mixture of 7-amino-1-[(1,3-dibenzoyloxy-2-propoxy)methyl]-1,3-azaphospholo[4,5-d]pyrimidine (compound 21, R=CH2OCH(CH2OBz)2, 0.65 g, 1.4 mmol) and methanolic ammonia (125 mL, saturated at 0° C.) was stirred at room temperature for 20 h. The solvent was evaporated under reduced pressure. The solid thus obtained was triturated with cold methanol (5 mL) and the product was collected by filtration. To the filtrate silica gel was added and the solvent was evaporated. The dry powder was loaded on top of a silica gel column (2×8 cm). The column was flash eluted with dichloromethane containing 0-25% methanol to give 0.28 g (78%) of the title compound, mp 180-182° C. Ir (KBr): ν695 (=P-C), 1215 (-P=CH), and 3060, 3300, 3380 and 3500 (NH2, OH) cm-1. Uv (pH 1): λmax254 nm (ε19,000), 282 (12,100), and 314 (4000); (MeOH): λmax266 nm (ε24,700), and 336 (24,000); (pH 11): 266 nm (ε27,650), and 340 (1900). 31 p nmr (DMSO-d6): δ 65.02. 1H nmr (DMSO-d6): δ 3.43 (m, 3 H, CH, CH2), 3.53 (m, 2 H, CH2), 4.63 (br s, 2 H, 2OH), 5.68 (s, 2 H, CH2), 8.23 (s, 2 H, NH2), 8.53 (d, I H, C5H), and 8.82 (d, 1 H, J =58.5 Hz, C2H ). Anal. Calcd. for C9H13N4O3P: C, 42.19; H, 5.11; N, 21.87. Found: C,42.37; H, 5.12; N, 21.66.

Provenance & Evidence