Sodium Bicarbonate → HCID 71274179, compound

Participants

Reaction Steps

To the solution of N-methoxy-N-methyl-5-((2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyrimidin-4-ylamino)methyl)-1,3,4-thiadiazole-2-carboxamide (17-1) (355 mg, 0.78 mmol) in THF (2 mL) was added CH3MgBr (1.3 mL, 3.90 mmol) in toluene dropwise at 0° C. The mixture was stirred for 30 min. Then the solution was adjusted to pH=9-10 with saturated sodium bicarbonate and extracted with ethyl acetate (20 mL*3). The organic layers were combined, dried over anhydrous sodium sulfate and purified by Prep TLC (PE/EA=1:1). The product was obtained as a white solid (248 mg, 77%). 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.37 (d, J=7.6 Hz, 1H), 7.03 (d, J=7.9 Hz, 1H), 5.59 (s, 1H), 5.42 (s, 1H), 4.99 (d, J=6.3 Hz, 2H), 4.28 (m, 2H), 2.79 (s, 3H), 2.44 (s, 3H), 2.28 (s, 3H), 2.07 (m, 1H), 1.89-1.81 (m, 1H), 1.32-1.27 (m, 1H), 1.04-1.02 (m, 1H); LRMS (ES) calculated M+H for C20H23N6O2S: 411.5. Found:411.1.

Provenance & Evidence