Water → HCID 86723901, compound

HRID 576791Notes

Reaction equation

HRID 576791 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][N:7]([C:30]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=2)[C:8]=1[C:9]1[C:10](=[O:29])[N:11]([CH:26]([CH3:28])[CH3:27])[C:12](=[O:25])[N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH:14]=1)(=[O:3])[CH3:2].[CH3:38][Mg]Cl.O.C(OCC)(=O)C>O1CCCC1>[OH:3][C:1]([C:4]1[CH:5]=[N:6][N:7]([C:30]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=2)[C:8]=1[C:9]1[C:10](=[O:29])[N:11]([CH:26]([CH3:28])[CH3:27])[C:12](=[O:25])[N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=2)[CH:14]=1)([CH3:38])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 86723902HCID 86723902, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 86723901HCID 86723901, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-acetyl-5-(3-isopropyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (prepared in Example 136) (28.2 mg) in tetrahydrofuran (1.0 ml) was added under ice-cooling methyl magnesium chloride (3.0 M tetrahydrofuran solution, 27.8 μl) dropwise and the resulting mixture was stirred under ice-cooling for one hour. To the resulting mixture was water (1 mL) followed by an addition of ethyl acetate (50 ml), and the mixture was washed with water (10 ml) and saturated saline (10 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 4-(4-(2-hydroxypropan-2-yl)-5-(3-isopropyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (4.3 mg) as white solid.

Workup

  1. temperaturecooling for one hour
  2. washthe mixture was washed with water (10 ml) and saturated saline (10 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-55cb0fff41504d1386bbd63a60f3a77f
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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