Water → HCID 57460697, compound

HRID 1674105Notes

Reaction equation

HRID 1674105 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[C:21](=[O:22])[N:20]([C:23]3[CH:35]=[CH:34][C:26]([O:27][CH:28]([CH3:33])[C:29](OC)=[O:30])=[CH:25][CH:24]=3)[C:19]([CH3:36])=[N:18][C:17]=2[CH2:37][CH2:38][CH3:39])=[CH:11][CH:10]=1)#[N:2].C(OCC)(=O)C.O>O1CCCC1>[OH:30][CH2:29][CH:28]([CH3:33])[O:27][C:26]1[CH:34]=[CH:35][C:23]([N:20]2[C:21](=[O:22])[C:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:4]4[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=4)=[CH:10][CH:11]=3)=[C:17]([CH2:37][CH2:38][CH3:39])[N:18]=[C:19]2[CH3:36])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 57460696HCID 57460696, compound

Product 1

HCID 57460697HCID 57460697, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-{5-[(2′-cyanobiphenyl-4-yl)methyl]-2-methyl-6-oxo-4-propylpyrimidin-1(6H)-yl}phenoxy]propanoate (1.60 g) in tetrahydrofuran (30 mL) was added lithium tetrahydroboron (80 mg), and the mixture was stirred at room temperature for 40 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 viscous substance (1.34 g, 88%).

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-52bada382b224fb0a9f61251cd62c6fe
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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