Methyl iodide → HCID 59674137, compound

HRID 1391533Notes

Reaction equation

HRID 1391533 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:32]=[CH:31][C:12]3[N:13]([CH3:30])[C:14]([N:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:33](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:33])[C:9]2[CH:32]=[CH:31][C:12]3[N:13]([CH3:30])[C:14]([N:16]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 59674250Tert-butyl 5-[(2-chloropyrimidin-4-yl)amino]-1-methyl-1H-benzimidazol-2-yl(phenyl)carbamate

Product 1

HCID 59674137HCID 59674137, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyl 5-[(2-chloropyrimidin-4-yl)amino]-1-methyl-1H-benzimidazol-2-yl(phenyl)carbamate (0.97 g, 2.2 mmol) was dissolved in DMF (10 ml) and cesium carbonate (2.15 g, 6.6 mmol) was added. After 15 min, iodomethane (0.20 ml, 3.3 mmol) was added, and the reaction was stirred at rt. After TLC showed the starting material to be consumed, the reaction was diluted with water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, dried over MgSO4 and concentrated to a red foam. The crude material was purified through silica gel to give the title compound as a white solid (0.80 g. 78% over two steps). 1H NMR (300 MHz, d6-DMSO) δ 7.90 (d, J=6.3 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.60 (d, J=1.8 Hz, 1H), 7.38 (m, 4H), 7.25-7.29 (m, 2H), 6.17 (d, J=5.7 Hz, 1H), 3.78 (s, 3H), 3.41 (s, 3H), 1.41 (s, 9H). MS (ESI) m/z=465 [M+H]+.

Workup

  1. customto be consumed
  2. additionthe reaction was diluted with water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a red foam
  7. customThe crude material was purified through silica gel

Sources & evidence

ORD record
ord-9f66503c4d1543d595d52e5d6b2910bb
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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