Triethylamine → HCID 9860535, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-2-formamido-9-[3-(isopropoxymethoxy)propoxy]purine (1.86 g, 5.40 mmol), 10% palladium on charcoal (190 mg), triethylamine (3.8 ml, 27 mmol) and methanol (30 ml) was stirred under an atmosphere of hydrogen at 20° C. for 4 hr. The suspension was filtered, the catalyst washed with chloroform and the combined filtrates evaporated under reduced pressure. The residue was dissolved in dichloromethane (50 ml), washed with saturated brine-water (2:1), dried (magnesium sulphate) and evaporated. The residue was dissolved in 0.5M sodium methoxide in methanol (21.6 ml) and heated at reflux for 1 hr. The solution was taken to neutrality using AMBERLITE IR 120(H) and evaporated. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (20:1) affording the title compound (630 mg, 41%) after recrystallisation from acetone-hexane; νmax (KBr) 3333, 3192, 1661, 1623, 1577, 1516, 1433 cm-1 ; δH [(CD3 )2SO] 1.09 (6H, d, J 6.05 Hz, 2×CH3), 1.95 (2H, quintet, J 6.6 and 6.3 Hz, CH2CH2CH2), 3.63 (2H, t, J=6.3 Hz, CH2OC), 3.77 (1H, septet, J=6.0 Hz, CH), 4.39 (2H, J=6.6 Hz, CH2ON), 4.64 (2H, s, OCH2O), 6.69 (2H, br.s, D2O exchangeable, NH2), 8.31 (1H, s, H-8), 8.59 (1H, s, H-6). Found: C, 51.21; H, 6.84; N, 24.82%; C12H19N5O3 requires: C, 51.22; H, 6.82; N, 24.89%.

Provenance & Evidence