Toluene → HCID 12096563, compound

HRID 2229788Notes

Reaction equation

HRID 2229788 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:12]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[N:11]=1.[F:31][C:32]([F:43])([F:42])[C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.C1(C)C=CC=CC=1>C(=O)([O-])[O-].[Na+].[Na+]>[F:31][C:32]([F:43])([F:42])[C:33]1[CH:38]=[C:37]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][NH:9][C:10]2[N:15]([CH3:16])[C:14](=[O:17])[C:13]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:12]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[N:11]=2)[CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 12096562HCID 12096562, compound

Product 1

HCID 12096563HCID 12096563, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

2-((2-bromophenylmethyl)amino)-5-(4-fluorophenyl)-6-(4-pyridyl)-3-methyl-4(3H)-pyrimidinone (175 mg, 0.38 mmol) was dipersed in 2M sodium carbonate solution (12 ml) and 3-trifluromethylbenzene-boronic acid (170 mg, 0.89 mmol), toluene (12 ml) were added to the above mixture and the reaction mixture was degassed and catalyst tetrakistriphenylphosphine Pd(0) (50 mg) was added. The reaction mixture was refluxed for 16 h. The formation of the product was monitored by TLC. Then it was cooled, diluted with toluene (12 ml) and washed with water. The organic layer was dried over sodium sulfate, concentrated and the product was purified by silica gel chromatgraphy to give the title compound. MS(m/z): 531.1 C30H22F4N4O requir. 530.53; 1H-NMR(CDCl3): d 8.43 (m, 2H, pyridyl), 7.69-7.12 (m, 8H, Ph), 7.11-6.88 (m, 6H, pyridyl and Ph—CF3), 4.85 (m, 3H, CH2—Ph and NH), 3.32(N—CH3)

Workup

  1. customthe reaction mixture was degassed
  2. additioncatalyst tetrakistriphenylphosphine Pd(0) (50 mg) was added
  3. temperatureThe reaction mixture was refluxed for 16 h
  4. temperatureThen it was cooled
  5. additiondiluted with toluene (12 ml)
  6. washwashed with water
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated
  9. customthe product was purified by silica gel chromatgraphy

Sources & evidence

ORD record
ord-9b31bffa97034c9595b6c2494bb48010
Source dataset
uspto-grants-2002_07
Patent number
US06420385B1

Reaction notes

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