HCID 15888040, compound → HCID 9837452, compound

Participants

Reaction Steps

A mixture of 7-amino-1-[(2-acetoxyethoxy)methyl]-1,3-azaphospholo[4,5-d]pyrimidine (compound 21, R=CH2OCH2CH2OAc, 0.45 g, 1.68 mmol) and methanolic ammonia (100 mL, saturated at 0° C.) was stirred at room temperature for 18 h. Methanolic ammonia was evaporated in vacuo and the residue was purified by silica gel column (2×8 cm) chromatography. The column was flash eluted with dichloromethane containing 0-12% methanol. The homogeneous fractions were pooled and evaporated to yield 0.35 g (92%) of the title compound, mp 165-166° C. Ir (KBr): ν705 (=P-C), 1210 (-P=CH), 2930, 3050, and 3270 (NH2, OH) cm-1. Uv (pH 1): λmax254 nm (ε24,200), 282 (15,200), and 312 (5000); (MeOH): λmax266 nm (ε28,900), and 340 (2300); (pH 11): 266 nm (ε34,700), and 340 (1900); 31 p nmr (DMSO-d6): δ 65.85; 1H nmr (DMSO-d6): δ 3.46 (m, 4 H, 2CH2), 4.70 (br s, 1 H, OH), 5.70 (s, 2 H, CH2), 8.52 and 8.69 (2s, 2 H, NH2), 8.65 (d, 1 H, C5H), and 8.96 (d, 1 H, J=54 Hz, C2H ). Anal. Calcd. for C8H11N4O2P.0.35 CH2Cl2 : C, 37.54; H, 4.61; N, 21.89. Found: C, 37.43; H, 4.13; N, 21.53.

Provenance & Evidence