Stannous chloride dihydrate → N1-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-yl)-4-methylbenzene-1,3-diamine

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Reaction Conditions

Reaction Steps

A suspension of 5-(4-(difluoromethoxy)phenyl)-N-(4-methyl-3-nitrophenyl)pyrimidin-2-amine 28a (1.5 mmol) and SnCl2.2H2O (4.5 mmol) in 1N NaHSO4 (50 mL) and 1,4-dioxane (50 mL) is heated at 100° C. for 1 h. The solvent is removed under vacuum and the residue dissolved in 5% NaOH and extracted with DCM (3×50 mL). The organic layer is washed with 5% NaOH (1×50 mL), water (1×50 mL), brine, dried over Na2SO4 and concentrated to afford N1-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-yl)-4-methylbenzene-1,3-diamine 29a which is used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 9.44 (s, 1H), 8.76 (s, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.8 Hz, 2H), 7.30 (t, J=74.4 Hz, 1H), 7.07 (d, J=2.0 Hz, 1H), 6.90 (dd, J=2.0, 8.0 Hz, 1H), 6.82 (d, J=8.4 Hz, 1H), 4.95 (bs, 2H), 2.02 (s, 3H). MS (m/z) (M+1)+: 343.1.

Provenance & Evidence