2-Methylmorpholine--hydrogen chloride (1/1) → 4-(2,3-Dichlorobenzyl)-2-(2-methylmorpholino)thiazolo[4,5-d]pyrimidin-7(4H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of triethylamine (2 drops), 2-methylmorpholine hydrochloride (16 mg, 0.154 mmol) and 4-(2,3-dichlorobenzyl)-2-(methylsulfonyl)thiazolo[4,5-d]pyrimidin-7(4H)-one (20 mg, 0.051 mmol) in DMF was stirred at 60° C. for 1 h. After cooled to ambient temperature, the mixture was diluted with water (10 mL) and extracted with dichloromethane (15 mL×3). The combined organic layers were washed with saturated brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (DCM:MeOH=20:1 elution) to give the desired product (8 mg, 38%) as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 8.49 (s, 1H), 7.63 (d, J=7.2 Hz, 1H), 7.35 (d, J=7.8 Hz, 1H), 7.16 (s, J=6.9 Hz, 1H), 5.46 (s, 2H), 3.88 (dd, J=12.3, 2.7 Hz, 1H), 3.77 (br, 2H), 3.55-3.47 (m, 2H), 3.31-3.20 (m, 1H), 2.94-2.89 (m. 1H), 1.13 (d, J=5.7 Hz, 3H); LC-MS: 411 (MH+); IR (thin film): 2976, 2920, 2855, 2360, 1627, 1605, 1555, 1495, 1444 cm−1.

Provenance & Evidence