Triethylamine → HCID 57460530, compound

HRID 1718628Notes

Reaction equation

HRID 1718628 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([CH3:36])[N:8]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]([OH:35])[CH3:34])[CH:28]=2)[C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:44]([Si:48](Cl)([CH3:50])[CH3:49])([CH3:47])([CH3:46])[CH3:45].C(OCC)(=O)C>CN(C)C1C=CN=CC=1.CN(C)C=O.O>[CH2:1]([C:5]1[N:6]=[C:7]([CH3:36])[N:8]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]([O:35][Si:48]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:50])[CH3:49])[CH3:34])[CH:28]=2)[C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 57460529HCID 57460529, compound

Product 1

HCID 57460530HCID 57460530, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-({4-butyl-1-[3-(1-hydroxyethyl)phenyl]-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl}methyl)biphenyl-2-carbonitrile (1.86 g), triethylamine (1.1 mL) and 4-dimethylaminopyridine (0.15 g) in N,N-dimethylformamide (20 mL) was added tert-butyl(chloro)dimethylsilane (0.88 g), and the mixture was stirred for 15 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, and the solvent was evaporated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (1.98 g, 86%).

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-6ece4754e24a427b9bcc3c43cad6e32f
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

Loading…