Methyl iodide → HCID 89783995, compound

Participants

Reaction Steps

To a 25-mL round-bottomed flask was added (R)-2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6-(hydroxymethyl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one and (S)-2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6-(hydroxymethyl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (469) (36 mg, 0.1 mmol), DMF (1 mL) and THF (1 mL). To the yellow suspension NaH (4 mg, 0.1 mmol, 60% in mineral oil) was added at RT. The reaction mixture was stirred at RT for 15 min and MeI (6 μt, 0.1 mmol) was added. The reaction mixture was stirred at RT for 1 h and the solvent was completely removed under vacuum. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 3-8% MeOH in DCM to provide 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6-(hydroxymethyl)-1-methyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (470) (28 mg, 75% yield, 50% ee) as a light yellow solid and a mixture of enantiomers. 1H NMR (400 MHz, DMSO-d6) δ 7.78 (dd, J=1.47, 8.12 Hz, 1H), 7.43-7.51 (m, 2H), 7.33-7.39 (m, 1H), 6.10 (s, 1H), 5.88 (s, 1H), 5.15 (t, J=5.38 Hz, 1H), 4.46 (t, J=6.16 Hz, 1H), 3.59 (t, J=5.97 Hz, 2H), 3.32 (s, 3H), 2.52 (s, 3H), 1.29 (s, 9H). m/z (ESI, +ve) 380.1 (M+H)+.

Provenance & Evidence