N,N-Dimethylethylenediamine → HCID 86723912, compound

HRID 576808

Reaction equation

HRID 576808 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2C(SC)=[CH:12][N:11]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([CH:23]=3)[C:21]#[N:22])[N:10]=2)=[C:5]([CH3:24])[N:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[C:3]1=[O:35].[Na].[CH3:37][S:38]([OH:40])=[O:39].[CH3:41]N(C)CCN>CS(C)=O.C(OCC)(=O)C.C1C=CC=CC=1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+].[Cu+]>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[C:37]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:12][N:11]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([CH:23]=3)[C:21]#[N:22])[N:10]=2)=[C:5]([CH3:24])[N:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:32])[F:33])[CH:26]=2)[C:3]1=[O:35]

Participants

7

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 1621282420277-69-4HCID 867239105-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylthio)-1H-pyrazol-1-yl)benzonitrile

Product 1

HCID 86723912HCID 86723912, compoundYield 41.4%

Reagents, catalysts & solvents 3

HCID 2734754Benzene;bis(copper(1+));bis(trifluoromethanesulfonate)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of the compound prepared in Example 269 (2.84 g) in dimethyl sulfoxide (9.8 ml) were added methanesulfinic acid sodium (2.00 g), copper trifluoromethanesulfonate benzene complex (1.24 g), N,N-dimethylethylenediamine (529 mg) and the resulting mixture was stirred at 110° C. for seven hours. The reaction mixture was diluted with ethyl acetate (300 ml), and the organic layer was washed with 10% ammonia water (50 ml) and saturated saline (50 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 4-(5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylsulfonyl)-1H-pyrazol-1-yl)benzonitrile (1.25 g).

Workup

  1. washthe organic layer was washed with 10% ammonia water (50 ml) and saturated saline (50 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-35e5bd401da64b9c8d637d157f70b4fa
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Linked notes

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