Methyl iodide → 4'-{[5-(4-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1719075Notes

Reaction equation

HRID 1719075 reaction equation
I[CH3:2].[H-].[Na+].[OH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[C:21](=[O:22])[N:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:26][CH:25]=4)[C:19]([CH2:38][CH2:39][CH3:40])=[N:18][C:17]=3[CH3:41])[CH:14]=2)[O:9][C:8]([CH3:43])([CH3:42])[CH2:7]1>CN(C)C=O.C(OCC)(=O)C>[CH3:2][O:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[C:21](=[O:22])[N:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:26][CH:25]=4)[C:19]([CH2:38][CH2:39][CH3:40])=[N:18][C:17]=3[CH3:41])[CH:14]=2)[O:9][C:8]([CH3:42])([CH3:43])[CH2:7]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 594694234'-{[5-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile

Product 1

HCID 594693994'-{[5-(4-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrileYield 66.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of iodomethane (0.76 g), 60% sodium hydride (0.22 g) and 4′-{[5-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile (0.56 g) in N,N-dimethylformamide (5 mL) was stirred for 1 hr. The reaction mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.38 g, 66%).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7bd2e13a980b46b2a3a625e7a8dafe45
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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