m-Chloroperbenzoic acid → 4'-(Cyclopropylmethyl)-N-methyl-2-(methylsulfinyl)-4,5'-bipyrimidin-2'-amine

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Reaction Steps

To a solution of 4′-(cyclopropylmethyl)-N-methyl-2-(methylsulfanyl)-4,5′-bipyrimidin-2′-amine (4-1) (770 mg, 2.68 mmol), m-CPBA (925 mg, 5.36 mmol) was added and the reaction mixture was stirred at rt for 2 hours. The reaction was partitioned between water and DCM. The organic layer was separated, and the aqueous layer was back-extracted. The organic extracts were combined, washed with brine, dried over sodium sulfate, then concentrated in vacuo. The crude product was purified by Biotage™ silica gel chromatography [50 g SNAP column, 100% DCM to 10% MeOH/DCM] to obtain a mixture of the desired product and the corresponding sulfone (645 mg, 79% yield). MS (ES+): m/z=304.2/305.2 (100/20) [MH+]. HPLC: tR=0.85 minute over 3 minutes. Purity: 73.2% [HPLC (LC/MS) at 220 nm].

Provenance & Evidence