HCID 14814185, compound → HCID 14814186, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-allyloxyamino-6-chloro-2.5-diformamido pyrimidine (1.23 g, 4.53 mmol) in diethoxymethyl acetate (20 ml) was stirred at 120° C. for 4 hours. The reaction was cooled and evaporated to dryness under reduced pressure. The residue was dissolved in methanol (5 ml) containing 0.88 ammonia (10 ml) and stirred at 25° C. for 16 hours. The solvents were evaporated under reduced pressure and the residue chromatographed on silica gel (eluted with ethyl acetate hexane 1:1) yielding the title compound (520 mg, 51%), m.p. 137°-9° C. UV: λmax (MeOH) 224 (ε 25,700). 247 (ε 5,300), 309 (ε 7.400) nm. IR: υmax (KBr) 3480, 3400. 3310, 3200, 1635, 1615, 1560, 1510, 1465 cm-1. 1H NMR δH [(CD3)2SO] 4.84 (2H, d, J=6 Hz, CH2ON), 5.35 (2H, m, CH2 =CH), 6.13 (1H, m, CH=CH2), 7.10 (2H, br.s, NH2), 8.35 (1H, s, H-8). Found: C, 42.45; H, 3.63; N, 30.39%; M+ 225.0406. C8H8Cl N5O requires C, 42.58; H, 3.57; N, 31.04%; M+ 225.0414.

Provenance & Evidence