Potassium Carbonate → 5-(6-chloropyrimidin-4-yloxy)-7-methyl-2-(trifluoromethyl)-1H-benzo[d]-imidazole
Reaction equation
[CH3:1][C:2]1[C:7]2[NH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:6]=2[CH:5]=[C:4]([OH:15])[CH:3]=1.[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C=O)C>[Cl:16][C:17]1[N:18]=[CH:19][N:20]=[C:21]([O:15][C:4]2[CH:3]=[C:2]([CH3:1])[C:7]3[N:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[NH:10][C:6]=3[CH:5]=2)[CH:22]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
57 mg (0.26 mmol) 7-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazol-5-ol and 46 mg (0.30 mmol) 4,6-dichloropyrimidine were placed in 2.0 mL DMF. 0.11 g (0.78 mmol) potassium carbonate were added and the mixture was stirred overnight at 70° C. The reaction mixture was combined with ice water. The substance was extracted with ethyl acetate and evaporated down i.vac. The crude product was purified by chromatography. The fractions containing product were combined and i evaporated down.vac. to leave the aqueous residue. This was neutralised with an aqueous 4M NaOH solution and extracted with ethyl acetate. The organic phase was evaporated down i.vac.
Workup
- extractionThe substance was extracted with ethyl acetate
- customevaporated down i.vac
- customThe crude product was purified by chromatography
- additionThe fractions containing product
- customi evaporated down.vac
- customto leave the aqueous residue
- extractionextracted with ethyl acetate
- customThe organic phase was evaporated down i.vac
Sources & evidence
- ORD record
- ord-f906213c7df143369801de08b9d52b0b
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952014B2
Reaction notes
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