Sodium Carbonate → (6-(3,4-Dichlorophenylamino)pyrimidin-4-yl)methanol

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Reaction Steps

BBr3 (0.399 ml, 4.22 mmol) was added dropwise to a stirred solution of N-(3,4-dichlorophenyl)-6-(methoxymethyl)pyrimidin-4-amine (0.3 g, 1.056 mmol) in DCM (4.0 mL) at 0° C. The mixture was further stirred for 30 min and poured onto ice water. The pH was adjusted to 10 using sat. Na2CO3 solution. The resulting suspension was extracted with ethyl acetate. The organic layer was isolated and dried over K2CO3 and concentrated to give (6-(3,4-dichlorophenylamino)pyrimidin-4-yl)methanol as a brown solid (0.275 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.05 (1H, br. s.), 8.92 (1H, s), 8.14 (1H, s), 7.71 (1H, d, J=8.78 Hz), 7.60 (1H, dd, J=8.78, 2.51 Hz), 7.05 (1H, s), 4.60 (2H, s). LCMS: R.T.=2.88; [M+H]+=271.96.

Provenance & Evidence