Ethanol → HCID 117759857, compound

HRID 709817Notes

Reaction equation

HRID 709817 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[N:12][C:13]([C:16]#N)=[N:14][CH:15]=1.S(=O)(=O)(O)[OH:24].[CH2:28]([OH:30])[CH3:29]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([O:18][CH2:19][CH:20]([CH3:21])[CH3:22])=[N:12][C:13]([C:16]([O:30][CH2:28][CH3:29])=[O:24])=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 117760267HCID 117760267, compound

Product 1

HCID 117759857HCID 117759857, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of 5-(2-fluoro-5-methoxyphenyl)-4-isobutoxypyrimidine-2-carbonitrile (1.00 g) in ethanol (25 mL) and water (8.3 mL) was added conc. sulfuric acid (25 mL) at 0° C., and the mixture was stirred at 120° C. for 1 hr. To the reaction mixture was added water at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (284 mg) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-195e064e168e42eca523144f15aa264a
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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