Methyl iodide → HCID 67498714, compound

HRID 1191633Notes

Reaction equation

[CH3:1][C:2]1[N:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:4]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:6]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C>[CH3:23][N:13]([N:3]1[CH:4]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:6]=[C:2]1[CH3:1])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-ylcarbamate (2.0 g, 7.3 mmol) in dry DMF (15 mL) at 0° C. was added sodium hydride (0.35 g, 8.7 mmol, 60% dispersion in oil). The reaction was stirred at 0° C. for 30 minutes and then methyl iodide (1.55 g, 10.9 mmol) was added portionwise. The reaction mixture was stirred at 0° C. for 3 hours before it was warmed to ambient temperature. The reaction was extracted with ethyl acetate (15 mL×2). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (1.18 g, 56.2%) as an orange oil, which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3): δ 8.96 (s, 1H), 8.49 (s, 1H), 8.16-8.13 (m, 1H), 7.38-7.36 (m, 2H), 3.36 (s, 3H), 2.35 (s, 3H), 1.44 (s, 9H); ESIMS m/z 289 [(M+H)]+.

Workup

stirringThe reaction mixture was stirred at 0° C. for 3 hours before it
temperaturewas warmed to ambient temperature
extractionThe reaction was extracted with ethyl acetate (15 mL×2)
washThe organic layer was washed with brine (10 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-e847456818a64788807d5c1e627ce75f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680121B2

Reaction notes

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