Methanol → HCID 54231036, compound

HRID 650626Notes

Reaction equation

HRID 650626 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH3:26])[C:8]([C:10]1[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=1)=[O:9].[CH3:36][OH:37]>>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH3:26])[C:8]([C:10]1[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][C:13]([O:37][CH3:36])=[N:14][CH:15]=1)=[O:9]

Participants

3

Reactant 2

HCID 887MethanolHCID 54164811HCID 54164811, compound

Product 1

HCID 54231036HCID 54231036, compoundYield 63.6%

Procedure

To a suspension of of 0.4 g (0.77 mmol) 2-methylsulfonyl-4-phenyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide in 10 ml methanol 0.10 g (1.93 mmol) sodiummethanolat (95%) was added. The reaction mixture was stirred for 16 hrs. After evaporation of the solvent, the residue was distributed between 50 ml CH2Cl2 and 50 ml H2O. The aqueous layer was extracted with 50 ml CH2Cl2, the combined organic layers dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 40:1) to give 0.23 g (63%) 2-methoxy-4-phenyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a colorless solid, m.p. 101.2-102°.

Workup

  1. additionwas added
  2. customAfter evaporation of the solvent
  3. extractionThe aqueous layer was extracted with 50 ml CH2Cl2
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 40:1)

Sources & evidence

ORD record
ord-55ecde4bae9c40878dcaf7fd90073805
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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