Triethylamine → HCID 24849198, compound

Participants

Reaction Steps

5-(5-(2-aminopyridin-4-yloxy)pyridin-2-yl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (128.6 mg, 0.333 mmol) was dissolved in THF (5.0 ml) and Et3N (0.10 ml, 0.72 mmol) and phenyl chloroformate (0.070 ml, 0.56 mmol) were added via syringe, and the reaction was stirred at room temperature. After about 45 minutes, pyrrolidine (0.31 ml, 3.7 mmol) was added, and the reaction was stirred at room temperature overnight. The next morning, the reaction was quenched with saturated ammonium chloride (5 ml) and extracted with DCM (3×15 ml). The organic phases were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel column (30:1->20:1 DCM/2 N ammonia in MeOH). The fractions with product collected, concentrated, washed with Et2O, and filtered. The solid collected was washed with Et2O and acetone and filtered again. The solid was collected and dried under vacuum to give the desired titled compound N-(4-(6-(1-methyl-6-oxo-2-(phenylamino)-1,6-dihydropyrimidin-5-yl)pyridin-3-yloxy)pyridin-2-yl)pyrrolidine-1-carboxamide (17.4 mg, 0.0360 mmol, 11% yield). MS (ESI pos. ion) m/z: 484 (MH+). Calc'd exact mass for C26H25N7O3: 483.

Provenance & Evidence