Potassium Carbonate → HCID 178509698, compound

HRID 474804Notes

Reaction equation

HRID 474804 reaction equation
[O:1]=[C:2]1[C:7]([CH2:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:6][NH:5][C:4](=[S:17])[NH:3]1.C([O-])([O-])=O.[K+].[K+].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38]Cl)=[CH:34][CH:33]=2)=[CH:27][C:26]=1[C:40]([F:43])([F:42])[F:41]>CC(C)=O>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:33]=[CH:34][C:35]([CH2:38][S:17][C:4]3[NH:5][CH:6]=[C:7]([CH2:8][C:9]4[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=4)[C:2](=[O:1])[N:3]=3)=[CH:36][CH:37]=2)=[CH:27][C:26]=1[C:40]([F:41])([F:42])[F:43]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 668255374-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl etherHCID 86666218HCID 86666218, compound

Product 1

HCID 178509698HCID 178509698, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 4-[(4-oxo-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)methyl]benzonitrile (70 mg, 0.288 mmol) and K2CO3 (41.3 mg, 0.299 mmol) in acetone (6 mL), which was stirred at room temperature for 5 min was added 1-chloro-4-{[4-(chloromethyl)phenyl]oxy}-2-(trifluoromethyl)benzene (60 mg, 0.187 mmol) under argon. The mixture was heated at 60° C. for 3 h. Purification via MDAP then afforded the title compound (31 mg, 0.059 mmol, 31.4% yield). LCMS: rt=3.98 min, [M+H+]=528

Workup

  1. temperatureThe mixture was heated at 60° C. for 3 h
  2. customPurification via MDAP

Sources & evidence

ORD record
ord-7ff5e11b10754bb4863638954dea7cbd
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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