Triethylamine → (R)-2,4-Diamino-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)pyrimidine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a 50 mL pear flask were added (R)-1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethan-1-amine (0.5 g, 1.921 mmol) and 2,4-diamino-6-chloropyrimidine-5-carbonitrile (0.326 g, 1.92 mmol) in DMF (9.60 mL) to give a white suspension. To the suspension was added Et3N (0.535 mL, 3.84 mmol) and the mixture was stirred at 100° C. for 6 hours. The mixture was allowed to stand at RT overnight. Saturated aqueous sodium bicarbonate solution (100 mL) was added, and the mixture was extracted with EtOAc (3×). The organic layers were combined, dried over MgSO4, filtered, and concentrated. The damp residue was slurried in Et2O. The solids were collected on a fritted glass funnel and washed with Et2O. UPLC indicated the presence of a small impurity having a slightly shorter retention time than the desired product. The solids were dissolved in hot EtOH and recrystallized overnight to give the title compound as an off-white solid (340 mg, 45.0%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.39 (d, J=6.32 Hz, 3 H), 2.70-2.83 (m, 2 H), 3.05 (br s, 2 H), 3.72-3.91 (m, 7 H), 5.90 (quin, J=6.76 Hz, 1 H), 6.41 (s, 2 H), 6.45-6.53 (m, 2 H), 6.58 (s, 2 H), 7.51-7.61 (m, 1 H), 7.84 (s, 1 H); ESI-MS m/z [M+H]+ calc'd for C19H23N9O, 394; found 394.

Provenance & Evidence