Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.[CH3:14][S:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH3:13][S:12][C:4]1[N:3]=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([S:15][CH3:14])=[CH:17][CH:18]=2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 4-chloro-2-methylthio-6-(trifluoromethyl)pyrimidine (ButtPark Ltd, 2.86 g, 14.55 mmol), 4-(methylthio)phenylboronic acid (Aldrich, 2.83 g, 1.1 eq), tetrakistriphenylphosphine palladium (0) (0.2 g) and sodium carbonate (4.04 g, 2.6 eq) in DME (200 ml) and water (100 ml) was heated under reflux with stirring under N2 for 24 h. The reaction mixture was concentrated in vacuo and the resultant mixture partitioned between ethyl acetate and water. The organic phase was separated, washed with water, dried (Na2SO4) and concentrated in vacuo to a purple solid. Purification by flash column chromatography with cyclohexane:ethyl acetate as (6:1) as eluant gave the title compound as a yellow crystalline solid (3.86 g, 84%).
Workup
- temperaturewas heated
- temperatureunder reflux
- concentrationThe reaction mixture was concentrated in vacuo
- customthe resultant mixture partitioned between ethyl acetate and water
- customThe organic phase was separated
- washwashed with water
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo to a purple solid
- customPurification by flash column chromatography with cyclohexane
Sources & evidence
- ORD record
- ord-5c5f310ae1454a24b63a9290631b748d
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780870B2
Linked notes
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