Ethanol → HCID 69199848, compound

Participants

Reaction Steps

To a round bottom flask fitted with a magnetic stirrer bar and rubber septum was added 2,4-bis(methylsulfonyl)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]-pyrimidine (Reference Example 5, Step A, 50 mg, 0.1 mmol), and 1 mL each of ethanol and acetonitrile. The mixture was cooled to 0° and methylamine (2 eq., 400 μL, 1M in THF) was added via syringe. The mixture was stirred for 1 h, the solvents removed under reduced pressure and the product chromatographed (77/23 hexanes/ethyl acetate) to give two products: a higher Rf product (unidentified) and 2-(3,4-difluorobenzyloxy)-4-(N-methylamino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine as the lower Rf product. HPLC/MS: m/e=442 (M+−1); Rt=3.58 min. 1H-NMR 500 MHz (CDCl3): δ 3.13 (d, J=5 Hz, 3H), 3.37 (s, 3H), 7.07 (d, J=8 Hz 1H), 7.10 (d, J=8 Hz, 2H), 7.18 (d, J=8 Hz, 1H), 7.38-7.40 (m, 3H).

Provenance & Evidence