Sodium Carbonate → 2-(Methylsulfanyl)-4-[4-(methylsulfanyl)phenyl]-6-(trifluoromethyl)pyrimidine

HRID 6695

Reaction equation

HRID 6695 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]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2480634-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidineHCID 27339594-(Methylthio)phenylboronic acid

Product 1

HCID 220183142-(Methylsulfanyl)-4-[4-(methylsulfanyl)phenyl]-6-(trifluoromethyl)pyrimidineYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

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 (3.869, 84%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe resultant mixture partitioned between ethyl acetate and water
  5. customThe organic phase was separated
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo to a purple solid
  9. customPurification by flash column chromatography with cyclohexane

Sources & evidence

ORD record
ord-32e67c2966e547bfa9726d4db0b83282
Source dataset
uspto-grants-2006_08
Patent number
US07084148B2

Linked notes

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