Water → HCID 12151212, compound

HRID 2415033Notes

Reaction equation

Cl[C:2]1[C:7]([I:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[N:5]=[C:4]([S:13][CH:14]([CH3:16])[CH3:15])[N:3]=1.[F:17][C:18]([F:30])([F:29])[C:19]1[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][NH:21][N:20]=1.O>CS(C)=O>[I:8][C:7]1[C:2]([N:21]2[CH:22]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([C:18]([F:17])([F:29])[F:30])=[N:20]2)=[N:3][C:4]([S:13][CH:14]([CH3:16])[CH3:15])=[N:5][C:6]=1[C:9]([F:12])([F:11])[F:10]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Chloro-5-iodo-2-isopropylthio-6-trifluoromethylpyrimidine (0.30 g) was dissolved in dimethylsulfoxide (3.0 ml) and ethyl 3-trifluoromethyl-1H-pyrazole-4-carboxylate (0.16 g) and 1,8-diazabicyclo-[5,4,0]-under-7-ene (0.12 g) was added at room temperature with stirring. The mixture was heated to 80° C. and stirred for 2 hr. After cooling to room temperature, the mixture was added water and extracted with benzene. The benzene layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give ethyl 1-(5-iodo-2-isopropylthio-6-trifluoromethylpyrimidin-4-yl)-3-trifluoromethyl-1H-pyrazole-4-carboxylate (0.30 g) as colorless crystalline solid, mp 107-108° C.

Workup

stirringstirred for 2 hr
temperatureAfter cooling to room temperature
extractionextracted with benzene
washThe benzene layer was washed with water and brine
dry with materialrespectively and dried over magnesium sulfate
customThe solvent was removed under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-f517ef110f194211bba8c05226b1cabb
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818631B1

Reaction notes

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