Methanol → HCID 178499130, compound

HRID 2053095Notes

Reaction equation

HRID 2053095 reaction equation
S(Cl)(Cl)=[O:2].C([O:12][C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:16]=[C:15]([C:29]#N)[N:14]=1)C1C=CC=CC=1.[CH3:31][OH:32]>>[CH3:31][O:32][C:29]([C:15]1[N:14]=[C:13]([OH:12])[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:16]=1)=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 588780594-Benzyloxy-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

Product 1

HCID 178499130HCID 178499130, compound

Procedure

To methanol (10 ml) at 0° C. was added thionyl chloride (500 ul). The mixture was stirred for 30 minutes then 4-benzyloxy-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (300 mg) was added and the reaction was heated to reflux for five hours. Solvent was evaporated under reduced pressure to yield crude product. Purification of the resulting residue by flash chromatography on silica afforded product 4-hydroxy-6-(3-trifluoromethylphenyl)-pyrimidine-2-carboxylic acid methyl ester (104 mg).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for five hours
  3. customSolvent was evaporated under reduced pressure
  4. customto yield crude product
  5. customPurification of the resulting residue by flash chromatography on silica afforded product 4-hydroxy-6-(3-trifluoromethylphenyl)-pyrimidine-2-carboxylic acid methyl ester (104 mg)

Sources & evidence

ORD record
ord-88029350f9954a2381d330aee223a8f6
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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