Diisopropylethylamine → 4-Chloro-6-[3-(diethoxyphosphorylmethoxy)propoxyamino]-5-formamidopyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of diethyl 3-aminooxypropoxymethylphosphonate (1.0 g, 4.15 mmol), 4,6-dichloro-5-formamidopyrimidine (0.80 g, 4.15 mmol) and diisopropylethylamine (2.16 ml, 12.45 mmol) in diglyme (25 ml) was heated at 100° C. for 2 h. The solvent was then removed in vacuo and the residue chromatographed in chloroform/methanol (50:1) to give 4-chloro-6-[3-(diethoxyphosphorylmethoxy)propoxyamino]-5-formamidopyrimidine (1.lg, 67%) as a brown oil; νmax (film) 1600, 1570, 1220, 1030 cm-1 ; δH [(CD3)2SO] 1.23(6H, t, J7.2 Hz, (CH3CH2O)2), 1.85(2H, m, CH2CH2CH2), 3.63(2H, t, J6 Hz, CH2OCH2P), 3.79(2H, d, J8.3 Hz, CH2P), 3.94(2H, t, J6.1Hz, CH2ON), 4.04(4 H, m, (CH3CH2O)2), 8.15(1H, s, H-2), 9.50(1H, br s, D2O exchangeable, NH), 10.50-12.00(1H, br s, NH); Found: C, 39.37; H, 5.69; N, 13.82%; M+ 396.0963; C13H22ClN4O6P requires: C, 39.35; H, 5.59; N, 14.12%; M+ 396.0966.

Provenance & Evidence