Water → HCID 58654363, compound

HRID 1170488Notes

Reaction equation

HRID 1170488 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[H-].[Na+].Cl[C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)[N:25]=1.O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)[N:25]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 229583304-Chloro-2-(1H-imidazol-1-yl)-6-methylpyrimidine

Product 1

HCID 58654363HCID 58654363, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of (benzhydrylidene-amino)-acetic acid ethyl ester (2.67 g, 10.0 mmol) in DMSO (50 mL) was added NaH (600 mg of a 60% dispersion on mineral oil, 15.0 mmol) slowly at r.t. under nitrogen and the mixture was stirred for 5 min. Then a solution of 4-chloro-2-imidazol-1-yl-6-methyl-pyrimidine (1.95 g, 10.0 mmol) in DMSO (15 mL) was added and the reaction mixture stirred at r.t overnight. Water was added and the solution was extracted with ethyl acetate, washed with brine and dried over Na2SO4. Evaporation of the solvent gave residue which was purified by column chromatography to give 1.30 g (31%) of (benzhydrylidene-amino)-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-acetic acid ethyl ester. [M+H]+ 426.18.

Workup

  1. stirringthe reaction mixture stirred at r.t overnight
  2. extractionthe solution was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent
  6. customgave residue which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-454abbfa41474606b60f0fd8d288ab20
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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