Sodium Carbonate → HCID 11190234, compound

HRID 354000Notes

Reaction equation

HRID 354000 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:6][N:7]([CH3:18])[C:8]([C:10]1[C:15](Br)=[CH:14][N:13]=[C:12]([CH3:17])[N:11]=1)=[O:9].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:6][N:7]([CH3:18])[C:8]([C:10]1[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:14][N:13]=[C:12]([CH3:17])[N:11]=1)=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 53758416HCID 53758416, compound

Product 1

HCID 11190234HCID 11190234, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 0.456 g (1 mmol) 5-bromo-2-methyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide, 0.034 g (0.2 mmol) tetrakis-(triphenylphosphin)palladium and 0.121 g (1 mmol) phenylboronic acid in 20 ml 1,2-dimethoxyethane a solution of 0.105 g (1 mmol) Na2CO3 in 8 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/MeOH 40:1) and crystallised (Ethanol) to give 0.258 g (57%) 2-methyl-5-phenyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as off-white crystalls, m.p. 149-152°.

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/MeOH 40:1)
  11. customcrystallised (Ethanol)

Sources & evidence

ORD record
ord-91ac2cec489e499e8b1f4ddc4950f079
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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