Diisopropylethylamine → (R)-N-(1-benzylpiperidin-3-yl)-N-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-1-benzyl-N-methylpiperidin-3-amine (800 mg, 3.9 mmol) and 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (1.2 g, 3.9 mmol) in DMF (10 mL), DIEA (2.02 mL, 15.6 mmol) was added and the reaction mixture was stirred at 60° C. overnight. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc (100 mL) and was washed with water (3×40 mL). The EtOAc layer was then dried over Na2SO4 and evaporated in vacuo to give a residue that was purified by column chromatography (silica gel, gradient EtOAc in hexanes) to afford the titled intermediate (750 mg, 40%). 1H-NMR (400 MHz, CDCl3): δ 8.37 (s, 1H), 8.02 (d, J=8.4 Hz, 2H), 7.38 (d, 0.1=4.0 Hz, 1H), 7.28 (m, 7H), 6.53 (d, J=3.6 Hz, 1H), 3.59 (d, J=13.2 Hz, 1H), 3.46 (d, J=13.2 Hz, 1H), 3.13 (s, 3H), 2.89 (m, 2H), 2.37 (s, 3H), 2.09 (t, J=10.8 Hz, 1H), 1.96 (dt, J=1.2, 10.8 Hz, 1H), 1.83 (m, 2H), 1.65 (m, 3H). LC-MS: m/z [M+1]=476.

Provenance & Evidence