Potassium Carbonate → HCID 15790823, compound

HRID 1417153Notes

Reaction equation

[C:1]([C:3]1[C:8](F)=[CH:7][C:6]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]=[CH:11]2)=[C:5]([F:21])[CH:4]=1)#[N:2].[CH2:22]([S:24]([NH2:27])(=[O:26])=[O:25])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:1]([C:3]1[C:8]([NH:27][S:24]([CH2:22][CH3:23])(=[O:26])=[O:25])=[CH:7][C:6]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]=[CH:11]2)=[C:5]([F:21])[CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4.3 g (14.3 mmol) of 3-(4-cyano-2,5-difluoro-phenyl)-6-trifluoromethyl-pyrimidin-4-one (cf. Example 1), 1.6 g (14.3 mmol) of ethanesulphonamide, 2.0 g (14.3 mmol) of potassium carbonate and 50 ml of dimethyl sulphoxide is stirred at 60° C. for 6 hours and then concentrated under reduced pressure. The residue is taken up in water and, after acidification, shaken with methylene chloride. The organic phase is dried with sodium sulphate and filtered. The filtrate is concentrated, and the crude product obtained as residue is purified by column chromatography (silica gel, ethyl acetate/chloroform, 1:1 by volume). 100 mg (2% of theory) of 3-(4-cyano-5-ethylsulphonylamino-2-fluoro-phenyl)-6-trifluoromethyl-pyrimidin-4-one of melting point 170° C. are obtained.

Workup

concentrationconcentrated under reduced pressure
stirringafter acidification, shaken with methylene chloride
dry with materialThe organic phase is dried with sodium sulphate
filtrationfiltered
concentrationThe filtrate is concentrated
customthe crude product obtained as residue
customis purified by column chromatography (silica gel, ethyl acetate/chloroform, 1:1 by volume)

Sources & evidence

ORD record: ord-7e2a0724dcc14e9285714c5787602e48
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05877121

Reaction notes

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