Sodium hydride → Ether isohexane

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (500 mg of a 60% suspension in mineral oil, 10 mmol) was added to a solution of with 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (2.02 g, 6.0 mmol) 2-diethyoxymethyl-5-aminopyrimidine (1.0 g, 5.0 mmol) in tetrahydrofuran (25 ml) and the reaction was heated at 70° C. for 2 hours. The reaction was cooled and excess sodium hydride quenched by the addition of methanol (1 ml) followed by concentration to dryness. The residue was dissolved in dichloromethane/methanol 20:1 (30 ml) and poured quickly through silica gel (20 g in a sinter funnel). Elution with dichloromethane/methanol 20:1 yielded 4-(2-diethoxymethyl-5-aminopyrimidine)-6-methoxy-7-(3-morpholinopropoxy)quinazoline after trituration with isohexane/ether (1:1) as an off-white solid (1.7 g, 70% yield):

Provenance & Evidence