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 1674406Notes

Reaction equation

HRID 1674406 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-338ae38208f543e9a2aca42db84765b1
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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