Tetrahydrofuran → HCID 57461009, compound

HRID 1719014Notes

Reaction equation

HRID 1719014 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH2:27][CH2:28][CH3:29])[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)[C:7](=[O:11])[C:8]=1[CH:9]=[O:10])[CH3:2].O1C[CH2:33][CH2:32][CH2:31]1>>[CH2:1]([C:3]1[N:4]=[C:5]([CH2:27][CH2:28][CH3:29])[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)[C:7](=[O:11])[C:8]=1[CH:9]([OH:10])[CH:32]([CH3:33])[CH3:31])[CH3:2]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 57460976HCID 57460976, compound

Product 1

HCID 57461009HCID 57461009, compoundYield 57%

Conditions

Temperature
-78 °C

Procedure

A mixture of 4′-[(4-ethyl-5-formyl-6-oxo-2-propylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile (0.6 g) and tetrahydrofuran (10 mL) was cooled to −78° C., isopropyl Grignard reagent tetrahydrofuran solution (1.0 M, 1.9 mL) was added dropwise, and the mixture was stirred for 1 hr. Then, the mixture was gradually warmed to room temperature, and the mixture was stirred for 12 hr. The solvent was evaporated from the reaction mixture under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.38 g, 57%).

Workup

  1. temperatureThen, the mixture was gradually warmed to room temperature
  2. stirringthe mixture was stirred for 12 hr
  3. customThe solvent was evaporated from the reaction mixture under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washThe diluted solution was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-efb7740de88e4114b2b51a26fdb3ccda
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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