Ethyl Acetate → HCID 71513633, compound

HRID 576782Notes

Reaction equation

HRID 576782 reaction equation
C([O:4][CH2:5][C@H:6]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[N:18]=[CH:17][CH:16]=2)=[C:11]([CH3:28])[N:10]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[C:9]1=[O:39])[CH3:7])(=O)C.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[OH:4][CH2:5][C@H:6]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[N:19]([C:20]3[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=3)[N:18]=[CH:17][CH:16]=2)=[C:11]([CH3:28])[N:10]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:37])([F:38])[F:36])[CH:30]=2)[C:9]1=[O:39])[CH3:7]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86723891HCID 86723891, compound

Product 1

HCID 71513633HCID 71513633, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-2-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-4-methyl-2,6-dioxo-3-(3-(trifluoromethyl)phenyl)-2,3-dihydropyrimidin-1(6H)-yl)propyl acetate (prepared in example 47) (31.9 mg) in ethanol (1.0 ml) was added under ice-cooling 1M aqueous sodium hydroxide solution (65.2 μl) and the resulting mixture was stirred for one hour under ice-cooling. To the reaction mixture was added ethyl acetate (100 ml) and the mixture was washed with 1M hydrochloric acid (30 ml) and saturated saline (30 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford (R)-4-(5-(3-(1-hydroxypropan-2-yl)-6-methyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (24.6 mg) as brown solid.

Workup

  1. temperaturecooling
  2. washthe mixture was washed with 1M hydrochloric acid (30 ml) and saturated saline (30 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d363296c27164cd3af0f5e4b9628e89b
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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