HCID 13989893, compound → HCID 13989894, compound

Participants

Reaction Conditions

Reaction Steps

6-(3-Benzyloxyprop-1-oxyamino)-4-chloro-2,5-diformamido pyrimidine (4.3 g, 11.3 mmol) in diethoxymethyl acetate (40 ml) was heated at 120° C. for 2.5 hours. The mixture was then cooled and evaporated to a syrup. The residue was dissolved in methanol (40 ml) and concentrated aqueous ammonia (5 ml). The solution was then stirred for 30 minutes at 20° C., evaporated under reduced pressure and the residue co-evaporated with methanol. Column chromatography on silica gel (eluted with chloroform-methanol, 50:1) gave the title compound (3.93 g, 95%) IR: υmax 3120, 3080, 1700, 1615, 1580, 1500, 1435 cm-1. 1H NMR: δH (CDC3) 2.15 (2H, quintet, J=6 Hz, CH2CH2CH2), 3.75 (2H, t, J=6 Hz, CH2OCH2Ph), 4.55 (4H, m, CH2ON, CH2Ph), 7.40 (5H, m, Ph), 8.10 (1H, s, H-8), 8.40 (1H, d, J=10 Hz, D2O exchangeable, NHCHO), 9.60 (1H, d, J=10 Hz, NHCHO).

Provenance & Evidence