Methanol → HCID 54290291, compound

HRID 353998Notes

Reaction equation

HRID 353998 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:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:13]=[C:12](S(C)(=O)=O)[N:11]=1)=[O:9].[CH3:36][OH:37].O>C(Cl)Cl>[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:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:13]=[C:12]([O:37][CH3:36])[N:11]=1)=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 54161888HCID 54161888, compound

Product 1

HCID 54290291HCID 54290291, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.45 g (0.87 mmol) 2-methanesulfonyl-5-phenyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide in 15 ml methanol 0.123 g (2.17 mmol) sodiummethanolate (95%) were added at RT and the reaction solution stirred for 12 hrs. The reaction mixture was distibuted between 100 ml H2O and 100 ml CH2Cl2. The aqueous layer was extracted three times with 50 ml CH2Cl2, the combined organic layers dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/methanol 40:1) to give 0.30 g (73%) 2-methoxy-5-phenyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a off-white solid, m.p. 97.5-98.5°.

Workup

  1. extractionThe aqueous layer was extracted three times with 50 ml CH2Cl2
  2. dry with materialthe combined organic layers dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2, CH2Cl2/methanol 40:1)

Sources & evidence

ORD record
ord-af98352727214103bea0f523bd456b0d
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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