Diisopropylethylamine → 5-{1-[(3,5-dichlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Participants

Reaction Steps

A solution of 5-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 2HCl (250 mg, 0.739 mmol), 5-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (250 mg, 0.739 mmol), HATU (281 mg, 0.739 mmol), DIEA (0.516 mL, 2.96 mmol) was stirred at room temperature overnight. LCMS indicated good conversion, so the reaction mixture was poured into water (10 mL), whereupon a precipitate formed. The precipitate was filtered and washed with water (10 ml) and dried at the pump for an hour. The residual pale green solid was adsorbed onto silica and purified by flash chromatography (100% EtOAc to 10% MeOH in EtOAc, 12-g column) to afford 5-{1-[(3,5-dichlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (285 mg, 85% yield) as a white solid. LC-MS (ES) m/z=452, 454 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 3.25 (t, J=8.3 Hz, 2H), 3.74 (s, 3H), 3.95 (s, 2H), 4.24 (t, J=8.5 Hz, 2H), 6.25-5.87 (br. s, 2H), 7.28-7.20 (m, 2H), 7.33 (s, 1H), 7.39 (d, J=1.8 Hz, 2H), 7.52 (d, J=1.8 Hz, 1H), 8.11 (d, J=8.1 Hz, 1H), 8.15 (s, 1H).

Provenance & Evidence