Diisopropylethylamine → 4-Chloro-6-[[3-(diethoxyphosphoryl)propoxy]amino]-2,5-diformamidopyrimidine

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Reaction Conditions

Reaction Steps

A mixture of 4,6-dichloro-2,5-diformamidopyrimidine (1.48 g, 6.3 mmol), diethyl 3-(aminooxy)propylphosphonate (1.33 g, 6.3 mmol), diisopropylethylamine (2.19 ml, 12.6 mmol) in diglyme (20 ml) was heated at 100° C. for 11/2 hours. After cooling, the solvent was removed under reduced pressure. The residue was chromatographed on silica gel (dichloromethane-methanol (97:3) as eluant) to give the title compound as a yellow foam (1.15 g, 58% based on recovered pyrimidine). 1H NMR: δH ((CD3)2SO+D2O) 1.21 (6H, t, J=7Hz, (OCH2CH3)2), 1.65-2.00 (4H, m, CH2CH2P), 3.85-4.05 (6H, m, N--OCH2, (OCH2CH3)2), 7.90+8.15 (1H, 5-NHCHO), 9.25 (2-NHCHO) Found: C, 38.12; H, 5.15; N, 16.25%. C13H21N5O6PCl requires: C, 38.10; H, 5.17; N, 17.09%.

Provenance & Evidence