HCID 14814204, compound → HCID 14814207, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-4-chloro-2,5-diformamido-6-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxyamino)pyrimidine 11 (900 mg, 2.6 mmol) in diethoxymethyl acetate (20 ml) was stirred at 120° C. for 3 hours. The solvent was removed under reduced pressure, the residue dissolved in methanol (20 ml) containing 0.88 ammonia solution (0.5 ml) and the mixture stirred for 1 hour at 25° C. The solvents were evaporated under reduced pressure and the residue chromatographed on silica, eluting with ethyl acetate-hexane (2:1), affording (R)-6-chloro-9-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)-2-formamidopurine (530 mg, 62%), m.p. 145°-8° C. UV: λmax (MeOH) 232 (ε 26,800), 291 (ε 9,600)nm; 1R: υmax (nujol) 1700, 1600, 1580 cm-1 ; 1H NMR: δH (CDCl3) 1.37 (3H,s, CH3), 1.42 (3H s, CH3), 3.87 (1H, m, CH2OC), 4.12 (1H, m, CH2OC), 4.46 (3H, m, CH+CH2ON), 8.20 (1H, s, H-8), 8.44 (1H, br. d, J=11.5 Hz, D2O exchangeable, NH), 9.55 (1H, J=11.5 Hz, HCONH).

Provenance & Evidence