Water → HCID 58577387, compound

HRID 1044272Notes

Reaction equation

HRID 1044272 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:26](=[O:27])[NH:25][C:24]3[C:19]2=[N:20][CH:21]=[N:22][CH:23]=3)=[CH:14][CH:13]=1.I[CH2:29][CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH2:29]([N:25]1[C:24]2[C:19](=[N:20][CH:21]=[N:22][CH:23]=2)[N:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][C:3]3[N:2]([CH3:1])[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[N:4]=3)=[CH:13][CH:14]=2)[C:26]1=[O:27])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 58577389HCID 58577389, compound

Product 1

HCID 58577387HCID 58577387, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 9-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-7,9-dihydro-8H-purin-8-one (56 mg), iodoethane (20 μL) and cesium carbonate (120 mg) in DMF (3 ml) was stirred at 50° C. for 4 h. The mixture was poured into water, and the mixture was extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residual crystals were recrystallized from AcOEt to give 7-ethyl-9-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-7,9-dihydro-8H-purin-8-one (40 mg) as white crystals.

Workup

  1. extractionthe mixture was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residual crystals were recrystallized from AcOEt

Sources & evidence

ORD record
ord-751fa509011640a3a222a6b1616d335d
Source dataset
uspto-grants-2013_10
Patent number
US08563575B2

Reaction notes

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