N,N-Dimethylaniline → HCID 178435386, compound

Participants

Reaction Conditions

Reaction Steps

Phosphorous oxychloride (21 mL) was carefully added to a mixture of 5.66 g (27.0 mmol) of 1,7-dihydro-6-ethyl-2-(methylthio)-4H-pyrrolo[2,3-d]pyrimidin-4-one and 1.70 mL of N,N-dimethylaniline. The reaction was heated to 95° C. for 12 hours. At this time the reaction was cooled and concentrated under vacuum. The residue was combined with 60 g of ice and stirred for 1 hour. The solids were collected by filtration, washed with 30 mL of water and suspended in 100 mL of water. The solids were again collected, washed with 30 mL of water, and dried in vacuo (40° C., 10 torr) to provide 5.50 g (89.6%) of 2-(methylthio)-4-chloro-6-ethyl-1H-pyrrolo[2,3-d]pyrimidine as a yellow solid. nmr (500 MHz, dmso-d6) δ1.24 (t, J=7.5 Hz, 3H), 2.52 (s, 3H), 2.70 (q, J=7.5 Hz, 2H), 6.21 (s, 1H), 12.27 (s, 1H)

Provenance & Evidence