Sodium hydride → HCID 59603511, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl-5-fluoroindole (0.164 g) in DMF (6 mL) was cooled to 0° C. then sodium hydride (0.066 g) added. After 30 min [1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-dimethyl-amine (0.395 g) was added. The reaction vessel was sealed and heated at 150° C. After 3 h the reaction mixture was cooled to room temperature and diluted with water and saturated aqueous sodium chloride solution. The resulting residual oil was separated from the aqueous layer, and then purified by chromatography (silica, 0 to 20% of a 49:1 MeOH:NH4OH mixture in dichloromethane) to furnish 119 (0.053 g, 10%) as a yellow solid. MS m/e 509 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.33-1.57 (m, 2H) 1.74 (d, 2H) 2.08 (t, 3H) 2.18 (s, 6H) 2.64 (s, 3H) 2.95 (d, 2H) 3.74-3.87 (m, 6H) 3.89-4.04 (m, 4H) 6.42 (s, 1H) 6.98-7.20 (m, 1H) 7.37 (m, 1H) 7.43 (s, 1H) 8.03 (m, 1H).

Provenance & Evidence