Diethyl Sulfate → HCID 57460766, compound

HRID 1674153Notes

Reaction equation

HRID 1674153 reaction equation
[OH:1][C:2]1[N:3]=[C:4]([CH3:24])[NH:5][C:6](=[O:23])[C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].S(OCC)(O[CH2:35][CH3:36])(=O)=O.CN(C)C=O>C(OCC)(=O)C>[CH2:35]([O:1][C:2]1[N:3]=[C:4]([CH3:24])[NH:5][C:6](=[O:23])[C:7]=1[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][CH:14]=1)[CH3:36]

Participants

6

Reactant 4

HCID 6163Diethyl SulfateHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 57460763HCID 57460763, compound

Product 1

HCID 57460766HCID 57460766, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4′-[(4-hydroxy-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (1 g), cesium carbonate (3.01 g), diethyl sulfate (0.41 mL) and N,N-dimethylformamide (20 mL) was stirred at 0° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogen sulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.17 g, 16%).

Workup

  1. washwashed with 5% aqueous potassium hydrogen sulfate solution
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-edb8c082b07a40d0b23366e547c2c301
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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