Sodium Carbonate → HCID 53929061, compound

HRID 353994Notes

Reaction equation

HRID 353994 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][N:7]([CH3:19])[C:8]([C:10]1[C:15](Br)=[CH:14][N:13]=[C:12]([S:17][CH3:18])[N:11]=1)=[O:9].[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][N:7]([CH3:19])[C:8]([C:10]1[C:15]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:14][N:13]=[C:12]([S:17][CH3:18])[N:11]=1)=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 54437820HCID 54437820, compound

Product 1

HCID 53929061HCID 53929061, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 3.50 g (7.17 mmol) 5-bromo-2-methylsulfanyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide, 0.213 g (0.2 mmol) tetrakis-(triphenylphosphin)palladium and 0.96 g (7.89 mmol) phenylboronic acid in 40 ml 1,2-dimethoxyethane a solution of 0.83 g (7.89 mmol) Na2CO3 in 15 ml H2O was added. The resulting reaction mixture was heated at reflux for 16 hrs. After evaporation of the 1,2-dimethoxyethan, the aqueous phase was extracted twice with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 40:1) and crystallised to give 2.4 g (69%) 2-methylsulfanyl-5-phenyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as off-white crystalls, m.p 109.7-110.7°.

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for 16 hrs
  5. customAfter evaporation of the 1,2-dimethoxyethan
  6. extractionthe aqueous phase was extracted twice with 50 ml CH2Cl2
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 40:1)
  11. customcrystallised

Sources & evidence

ORD record
ord-1aa3efde3b0e4f83b00867c3c0c225ae
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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