Potassium Carbonate → Methyl 3-methoxy-4-({6-[4-(methylsulfonyl)phenyl]-5-(4-fluorophenyl)-2-(trifluoromethyl)pyrimidin-4-yl}oxy)benzoate

HRID 72683

Reaction equation

HRID 72683 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[C:6]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[N:5]=[C:4]([C:25]([F:28])([F:27])[F:26])[N:3]=1.[C:29]([O:40][CH3:41])(=[O:39])[C:30]1[CH:38]=[CH:37][C:35]([OH:36])=[C:32]([O:33][CH3:34])[CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:34][O:33][C:32]1[CH:31]=[C:30]([CH:38]=[CH:37][C:35]=1[O:36][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[C:6]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[N:5]=[C:4]([C:25]([F:28])([F:27])[F:26])[N:3]=1)[C:29]([O:40][CH3:41])=[O:39]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 19844Methyl VanillateHCID 99105864-Chloro-5-(4-fluorophenyl)-6-[4-(methylsulfonyl)phenyl]-2-(trifluoro methyl)pyrimidine

Product 1

HCID 24962320Methyl 3-methoxy-4-({6-[4-(methylsulfonyl)phenyl]-5-(4-fluorophenyl)-2-(trifluoromethyl)pyrimidin-4-yl}oxy)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Chloro-5-(4-fluorophenyl)-6-[4-(methylsulfonyl)phenyl]-2-(trifluoro methyl)pyrimidine (0.5 g, 1.63 mmol), methyl vanillate (0.423 g, 2.33 mmol), potassium carbonate (0.24 g, 1.74 mmol) and acetonitrile (7 ml) were stirred at room temperature for 2 hours and subsequently the reaction mixture was refluxed for 6 hours. Further, potassium carbonate (0.08 g, 0.58 mmol) and vanillic ester (0.12 g, 0.66 mmol) were added to the reaction mixture and the refluxing was continued for another 4 hours. Subsequently the reaction mixture was poured onto ice-cold water, extracted with ethyl acetate (25 mL) and washed with brine solution. Evaporation of the organic layer yielded the required product. 1H-NMR (DMSO-d6) δ: 3.24 (s, 3H), 3.81 (s, 3H), 3.88 (s, 3H), 7.26-7.30 (m, 2H), 7.44 (d, 1H), 7.49-7.53 (m, 2H), 7.61-7.69 (m, 4H), 7.91 (d, 2H); MS m/z: 576.8 (M++1).

Workup

  1. temperaturesubsequently the reaction mixture was refluxed for 6 hours
  2. additionSubsequently the reaction mixture was poured onto ice-cold water
  3. extractionextracted with ethyl acetate (25 mL)
  4. washwashed with brine solution
  5. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-4aacb8644ab84cc98c344539e0d96b15
Source dataset
uspto-grants-2014_09
Patent number
US08828999B2

Linked notes

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