HCID 11371703, compound → HCID 12037374, compound

HRID 897411Notes

Reaction equation

HRID 897411 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[C:5]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[N:4]=[C:3]1[C:25]#N>C1COCC1>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:17])([F:16])[F:18])[CH:10]=2)=[C:5]([C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)[N:4]=[C:3]1[CH2:25][CH2:6][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 11371703HCID 11371703, compound

Product 1

HCID 12037374HCID 12037374, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methyl-4-oxo-6-(4-pyridyl)-5-(3-(trifluoromethyl)-phenyl)-3H-pyrimidine-2-carbonitrile (280 mg, 0.79 mmole) in THF (20 mL) was added phenethylene magnesium chloride (1.0M in THF, 1.2 mL) at 0° C. The reaction solution was then stirred at 0° C. for 5 mins. The mixture was partitioned between sat. ammonium chloride and ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and concentrated to a syrup. The residue was purified by column chromatography on silica gel (30% ethyl acetate in hexane) to give the product as a syrup; MS (m/z) 436(M+H)+; C25H20F3N3O requir. 435.4.

Workup

  1. customThe mixture was partitioned between sat. ammonium chloride and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a syrup
  6. customThe residue was purified by column chromatography on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6cd7f164070e4050b1537de281959469
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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