Water → HCID 178469905, compound

HRID 705853Notes

Reaction equation

HRID 705853 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][NH:5][C:4](=[S:13])[NH:3]1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28]Cl)=[CH:24][CH:23]=2)=[CH:17][C:16]=1[C:30]([F:33])([F:32])[F:31].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][S:13][C:4]3[NH:5][CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2](=[O:1])[N:3]=3)=[CH:26][CH:27]=2)=[CH:17][C:16]=1[C:30]([F:31])([F:32])[F:33]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 735952Ethyl 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarboxylateHCID 668255374-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl ether

Product 1

HCID 178469905HCID 178469905, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 4-oxo-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate (1.016 g, 5.07 mmol), 1-chloro-4-{[4-(chloromethyl)phenyl]oxy}-2-(trifluoromethyl)benzene (1.793 g, 5.58 mmol) and K2CO3 (0.771 g, 5.58 mmol) in DMF (15 mL) was heated with a microwave reactor at 80° C. for 0.5 h. The mixture was poured into 100 mL water and extracted with EA. The organic phase was dried over sodium sulfate, filtered, and concentrated to afford the title compound (2.461 g, 5.07 mmol, 100% yield). LCMS: rt=3.64 min, [M+H]=485

Workup

  1. extractionextracted with EA
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9a1a11db9e654ee8b492bdc7fd13dc1b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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