Formaldehyde → HCID 59849184, compound

Participants

Reaction Steps

To a solution of 7-[5-chloro-2-(2-methoxy-phenylamino)-pyrimidin-4-ylamino]-2-methyl-4-piperazin-1-yl-2,3-dihydro-isoindol-1-one (2.0 g, 4.17 mmol) in dichloroethane (50 mL), formaldehyde (380 μL, 5.0 mmol) is added and the mixture is stirred at room temperature for 1.5 hours. After addition of triacetoxy sodium borohydride (1.06 g, 5.0 mmol), the mixture is stirred at room temperature for 1.5 hours. The mixture is poured into 1N sodium hydroxide and stirred at room temperature for 10 min, then extracted twice with dichloromethane. The organic layer is successively washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The resulting solids are washed with methanol and ethyl acetate to give 7-[5-Chloro-2-(2-methoxy-phenylamino)-pyrimidin-4-ylamino]-2-methyl-4-(4-methyl-piperazin-1-yl)-2,3-dihydro-isoindol-1-one (1.2 g) as pale yellow solids in 58% yield. Rf=0.30 (MeOH/AcOEt=½). ESI-MS m/z: 494 [MH]+. 1H-NMR (400 MHz, CDCl3, δ, ppm): 2.38 (s, 3H), 2.66-2.57 (m, 4H), 3.09-3.07 (m, 4H), 3.21 (s, 3H), 3.92 (s, 3H), 4.37 (s, 2H), 6.92 (dd, 1H), 7.03-6.96 (m, 2H), 7.13 (d, 1H), 7.45 (s, 1H), 8.11 (s, 1H), 8.33 (dd, 1H), 8.67 (d, 1H), 10.5 (s, 1H).

Provenance & Evidence