Water → HCID 11524380, compound

HRID 1348993

Reaction equation

HRID 1348993 reaction equation
[CH3:1][O:2][C:3]1[C:4](S(C)(=O)=O)=[N:5][C:6]([N:9]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[N:10]2)=[N:7][CH:8]=1.[OH:22][C:23]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[S:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([O:22][C:23]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[S:25][CH:24]=2)=[N:5][C:6]([N:9]2[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[N:10]2)=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 110842734-Hydroxy-2-(trifluoromethyl)thiopheneHCID 12115990HCID 12115990, compound

Product 1

HCID 11524380HCID 11524380, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.4 g (1.24 mmol) of 5-methoxy-4-methylsulfonyl-2-(4-trifluoromethyl-1H-1-pyrazolyl)pyrimidine, 0.27 g (1.60 mmol) of 3-hydroxy-5-trifluoromethyl-thiophene and 0.34 g (2.47 mmol) of K2CO3 in 10 ml of DMF is stirred at 60° C. for 6 h and then at RT for 48 h. It is subsequently poured into 20 ml of water and extracted with four times 15 ml of CH2Cl2. The combined organic phase is dried over Na2SO4, filtered and concentrated. Chromatographic purification on silica gel with heptane/ethyl acetate (3:7) as eluent gives 0.3 g of 5-methoxy-2-(4-trifluoromethyl-1H-1-pyrazolyl)-4-(5-trifluoromethyl-3-thienyloxy)pyrimidine as colorless crystals.

Workup

  1. waitat RT for 48 h
  2. extractionextracted with four times 15 ml of CH2Cl2
  3. dry with materialThe combined organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification on silica gel with heptane/ethyl acetate (3:7) as eluent

Sources & evidence

ORD record
ord-c1671ce1ad6b441c8f8873f2c82ce678
Source dataset
uspto-grants-2007_05
Patent number
US07211673B2

Linked notes

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