Ammonia → HCID 178508034, compound

Participants

Reaction Conditions

Reaction Steps

Trans-N1-(benzo[d]thiazol-2-yl)-N3-(5-iodopyrimidin-4-yl)cyclobutane-1,3-diamine (synthesized analogous to intermediate 33 using 5-iodo-4-chloropyrimidine in place of 3-bromo-2-chloropyridine, 0.130 g, 0.307 mmol), copper (0.010 g, 0.157 mmol), and cesium acetate (0.250 g, 1.302 mmol) were suspended in dry dimethylsulfoxide (2 mL) in a microwave vessel. Ammonia (2.0 M solution in methanol, 1.0 ml, 2.000 mmol) was added and the mixture sealed under argon. It was heated at 80° C. in an oil bath for 4½ hours then cooled to 60° C. and stirred for another 14 hours. The reaction mixture was partitioned between ethyl acetate (200 mL), water (200 mL), and ammonium hydroxide (30 mL). The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (0-10% (2 N ammonia in methanol) in dichloromethane gradient) gave the desired N4-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)pyrimidine-4,5-diamine (0.033 g, 0.106 mmol, 34.4% yield).

Provenance & Evidence