Hydrochloric Acid → 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester

Participants

Reaction Steps

A suspension of 6-chloro-7-deazapurine (750 mg; 4.88 mmol), methyl 3-amino-2-thiophenecarboxylate (1.15 g; 7.33 mmol) and concentrated hydrochloric acid (410 μL; 4.9 mmol) in tert-butanol (15 mL) was microwaved at 75° C. for 3 h. The reaction mixture was diluted with methanol (15 mL) and filtered. The aqua solid was washed with methanol and dried under vacuo to afford the hydrochloric salt of 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester (900 mg, 59%) as a green-gray solid (HPLC: 99%, RT: 6.50 min). 1H NMR (DMSO-d6) 12.47 (br s, 1H), 10.68 (br s, 1H), 8.44 (s, 1H), 8.08 (br s, 1H), 8.02 (d, J=5.5 Hz, 1H), 7.47 (dd, J=3.3, 2.2 Hz, 1H), 6.66 (br s, 1H), 3.83 (s, 3H); MS (m/z) 275 [M+H]+.

Provenance & Evidence