Diethyl Sulfate → HCID 57460766, compound

HRID 1718823Notes

Reaction equation

HRID 1718823 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-d87ef7d93b05422d9102043d70b4a6c0
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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