Ethyl Acetate → HCID 57460869, compound

HRID 1674225Notes

Reaction equation

HRID 1674225 reaction equation
[OH:1][N:2]1[C:7](=[O:8])[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)=[C:5]([CH2:24][CH2:25][CH3:26])[N:4]=[C:3]1[CH3:27].[C:28]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:33]=CC=C[CH:29]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:61]([O:64][CH2:65][CH3:66])(=O)[CH3:62]>O1CCCC1.O>[CH3:62][C@@H:61]1[CH2:33][CH:28]([O:1][N:2]2[C:7](=[O:8])[C:6]([CH2:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]4[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:14][CH:15]=3)=[C:5]([CH2:24][CH2:25][CH3:26])[N:4]=[C:3]2[CH3:27])[CH2:29][C@H:65]([CH3:66])[O:64]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57460864HCID 57460864, compound

Product 1

HCID 57460869HCID 57460869, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4′-[(1-hydroxy-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (0.50 g), (2R,4s,6S)-2,6-dimethyltetrahydro-2H-pyran-4-ol (0.54 g) and triphenylphosphine (1.1 g) in tetrahydrofuran (5 mL) was added diisopropyl azodicarboxylate (2.2 mL, 1.9 M toluene solution), and the mixture was stirred for 1 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 colorless solid (0.62 g, 95%).

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-873d95d692a94db2a4ca48bdf3d06ae3
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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