Water → 5-methyl-2-(4-trifluoromethyl-1H-1-pyrazolyl)-4-(5-trifluoromethyl-3-thienyloxy)pyrimidine

HRID 1793769Notes

Reaction equation

[CH3:1][C:2]1[C:3](S(C)(=O)=O)=[N:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[N:9]2)=[N:6][CH:7]=1.[OH:21][C:22]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[S:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][C:2]1[C:3]([O:21][C:22]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[S:24][CH:23]=2)=[N:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=[N:9]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 0.8 g (2.6 mmol) of 5-methyl-4-methylsulfonyl-2-(4-trifluoromethyl-1H-1-pyrazolyl)pyrimidine, 0.44 g (2.6 mmol) of 3-hydroxy-5-trifluoromethylthiophene and 0.72 g (5.2 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 0.5 g of 5-methyl-2-(4-trifluoromethyl-1H-1-pyrazolyl)-4-(5-trifluoromethyl-3-thienyloxy)pyrimidine as colorless crystals.

Workup

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

Sources & evidence

ORD record: ord-e171cb9b172342bf8e5dc9c1b28db028
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022650B2

Reaction notes

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