Water → HCID 57460946, compound

HRID 1718960Notes

Reaction equation

HRID 1718960 reaction equation
[CH3:1][C:2]([CH3:38])([O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17](=[O:18])[C:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[C:27]([C:32]#[N:33])=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:22][CH:21]=3)=[C:15]([CH2:34][CH2:35][CH3:36])[N:14]=[C:13]2[CH3:37])=[CH:8][CH:7]=1)[CH:3]=[O:4].[CH3:39][Mg]Br.C(OCC)(=O)C.O>O1CCCC1>[OH:4][CH:3]([CH3:39])[C:2]([CH3:38])([CH3:1])[O:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:17](=[O:18])[C:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[C:27]([C:32]#[N:33])=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:22][CH:21]=3)=[C:15]([CH2:34][CH2:35][CH3:36])[N:14]=[C:13]2[CH3:37])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 57460945HCID 57460945, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57460946HCID 57460946, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4′-({1-[4-(1,1-dimethyl-2-oxoethoxy)phenyl]-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl}methyl)biphenyl-2-carbonitrile (1.15 g) in tetrahydrofuran (10 mL) was added methylmagnesium bromide (3.0 M diethyl ether solution, 0.78 mL) at −78° C., and the mixture was stirred for 3 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.60 g, 74%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-73e77254dea84d8ea69af117beaf32f0
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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