Dimethyl Sulfoxide → HCID 16066664, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-[5-chloro-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl]-4-methylpyridin-2-ylamine from step 5 (5.42 g, 166 mmol), isonipecotic acid (85.9 g, 665 mmol), cesium carbonate (162 g, 498 mmol), and DMSO (55 mL) was heated, with stirring, at 125° C. After 20 h, the mixture was cooled to 20° C. and water (165 mL) was added. The mixture was stirred for 15 min and was then treated with ethyl acetate (55 mL). The layers were separated and the aqueous was treated with another portion of ethyl acetate (55 mL). The layers were separated again and the aqueous layer was taken to pH ˜5 using 6 M HCl. After stirring for 1 hour, the resulting solid was filtered, washed with water (20 mL) and dried in vacuuo, to give 5.5 g of the title compound. 1H NMR (400 MHz, DMSO-d6): 1.10 (t, 3 H), 1.30 (t, 3 H), 1.49-1.60 (m, 2 H), 1.84-1.95 (m, 2 H), 2.32-2.36 (m, 3 H), 2.52-2.57 (m, 1 H), 2.78 (q, 2 H), 2.99-3.08 (m, 2 H), 3.52 (q, 2 H), 3.78 (t, 2 H), 4.45-4.53 (m, 2 H), 4.56-4.64 (m, 2 H), 6.91 (d, 1 H), 8.05 (s, 1 H), 8.18 (d, 1 H), 9.63 (s, 1 H), 12.18 (s, 1 H). LCMS m/z 454.

Provenance & Evidence