Hydrochloric Acid → 4-[4-(Methylthio)phenyl]-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

HRID 72689Notes

Reaction equation

HRID 72689 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:30][S:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.Cl>C1(C)C=CC=CC=1>[CH3:30][S:31][C:32]1[CH:37]=[CH:36][C:35]([C:2]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[N:3]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 104046804-Chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

Product 1

HCID 249575454-[4-(Methylthio)phenyl]-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidine (0.2 g, 0.6 mmol, prepared according to the procedure described in PCT/IB03/02879) was heated to reflux with tetra-kis triphenyl palladium (0) (0.068 g, 0.058 mmol), aqueous solution of potassium carbonate (0.16 g in 0.16 ml water), 4-(methylthio)benzene boronic acid (0.168 g, 1 mmol) and toluene (20 ml) under a nitrogen atmosphere overnight. The reaction mixture was acidified with dilute hydrochloric acid 10 ml and extracted with ethyl acetate. The organic layer was concentrated; the crude material obtained was triturated with ether and filtered to yield the title compound. 1H-NMR (DMSO-d6) δ: 2.45 (s, 3H), 7.13-7.15 (m, 4H), 7.23-7.34 (m, 8H), 7.61 (d, 2H); MS m/z: 423.1 (M++1).

Workup

  1. temperaturewas heated
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customthe crude material obtained
  5. customwas triturated with ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-54bb48fc0554462a96207235fc6b2728
Source dataset
uspto-grants-2014_09
Patent number
US08828999B2

Reaction notes

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