Sodium hydride → HCID 178504255, compound

Participants

Reaction Steps

To a solution of sulfone 11.1 (3.0 g, 8.87 mmol) in 10 mL of 1-methyl-2-pyrrolidinone was added 60% sodium hydride (390 mg, 9.76 mmol, mineral oil). The reaction was stirred for 15 minutes at room temperature and then 2-(trimethylsilyl)ethoxymethyl chloride (1.57 mL, 8.87 mmol) was added. The reaction was stirred at room temperature for 4 hours. To this solution was then added 5.06 g of trans-1,4-diaminocyclohexane predissolved in 15 mL 1-methyl-2-pyrrolidinone. The reaction was then warmed to 60° C. for 24 hours. The reaction was poured into brine and the product extracted into ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate and water, dried over magnesium sulfate, and concentrated in vacuo to give a light brown oil. Purification by chromatography using 2% methanol/dichloromethane to 5% methanol/dichloromethane as eluant gave 2.8 g of 7-(trans-4-aminocyclohexylamino)-3-(2-chlorophenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a pale yellow foam. (MH+=502).

Provenance & Evidence