Methanol → HCID 59753959, compound

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Reaction Steps

To a round bottom flask fitted with a magnetic stir bar and small reflux condenser was added 0.25 mL methanol, sodium metal (23 mg, 1.0 mmol). The flask was flushed with nitrogen. When the sodium dissolved, 2,4-bis(methylthio)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]-pyrimidine (Reference Example 4, 215 mg, 0.5 mmol) in 500 μL methanol was added by syringe. The methanol was removed under high vacuum and 2 mL scrupulously dried DMF (15X sieve and 3A sieve, respectively) added to the mixture. The mixture was stirred for 5 h, quenched in aqueous NH4Cl and immediately extracted with ether. Starting material and product were observed by LC. The organic layer was dried over MgSO4 and filtered. The solvent removed under reduced pressure. Flash column chromatography on silica gel (eluted with 98/2 hexanes/ethyl acetate) gave pure product and mixed starting material/product fraction. The title compound eluted by LC at Rt=4.62 min, m/e=313 (M++1). 1H-NMR 500 MHz (CDCl3): δ 2.64 (s, 3H), 4.05 (s, 3M), 7.08 (d, J=8 Hz, 2H), 7.13 (d, J=8 Hz, 1H), 7.19-7.24 (m, 3H), 7.34 (d, J=2 Hz, 1H).

Provenance & Evidence