Methylamine → 4,6-Dichloro-n-methylpyrimidin-2-amine

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Reaction Steps

Methylamine (2M solution, 113 mL, 217 mmol, 2.05 equiv) was charged to a 1 L 3-neck flask fitted with a magnetic stirrer and a thermometer. The mixture was chilled in an ice bath. To this stirred solution was added via addition funnel a solution of 4,6-dichloro-2-(methylsulfonyl)pyrimidine (25 g, 110 mmol) in EtOAc (250 mL) portionwise over a 25 minutes period. The temp was between 5-10° C. After completion of addition, the ice bath was removed, and the mixture was stirred for 1 hour at ambient temperature. LCMS showed conversion complete. The suspension was filtered, and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was partitioned between water (100 mL) and EtOAc (450 mL). The organic was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give white solids, which were triturated in 150 mL of CH2Cl2. These solids were collected by filtration and washing with cold CH2Cl2 (50 mL). Drying under house vacuum at room temperature for 20 hours, and then high vacuum at room temperature for 3 hours gave 9.31 g of the title compound as a solid. LC-MS (ES) m/z=179 [M+H]+.

Provenance & Evidence