Sodium Hydroxide → HCID 136344410, compound

Participants

Reaction Steps

A solution of 4-[4-(7-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-piperazin-1-yl]-benzoic acid ethyl ester (163 mg, 427 μmol) in tetrahydrofuran (1.6 mL) and methanol (0.8 mL) was treated with a 1N aqueous sodium hydroxide solution (748 μL, 748 μmol). The resulting yellow solution was stirred for 3 h at room temperature. At this point, another aliquot of a 1N aqueous sodium hydroxide solution (748 μL, 748 μmol) was added. At this time, the reaction was heated to 75° C. where it was stirred for 1.5 h. The reaction was then diluted with water (10 mL) and extracted with ethyl acetate (20 mL). The aqueous layer was acidified to pH 2 with a 1N aqueous hydrochloric acid solution and further extracted with ethyl acetate (20 mL). The organic layer was washed with a saturated aqueous sodium chloride solution (10 mL). Since product was not soluble in the organic layer, all of the layers were combined and concentrated in vacuo and dried to afford 4-(4-(7-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)piperazin-1-yl)benzoic acid (193 mg, 128%) as a light grey solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.41 (br. s., 4H) 3.57 (s, 3H) 3.71 (br. s., 4H) 6.25 (d, J=3.39 Hz, 1H) 6.78 (d, J=3.39 Hz, 1H) 7.02 (d, J=9.23 Hz, 2H) 7.79 (d, J=8.85 Hz, 2H) 10.89 (s, 1H) 12.29 (s, 1H). LC-MS calcd. for C18H20N5O3 [(M+H)+] 354, obsd. 354.1.

Provenance & Evidence