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Sodium Carbonate → 2-Methylsulfanyl-4-(4-trifluoromethylphenyl)pyrimidine

HRID 1269623
Notes
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Reaction equation

HRID 1269623 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>C(COC)OC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][S:8][C:4]1[N:3]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=2)[CH:7]=[CH:6][N:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 971134-Chloro-2-methylthiopyrimidineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 184483552-Methylsulfanyl-4-(4-trifluoromethylphenyl)pyrimidine

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-chloro-2-methylthiopyrimidine (2.17 mL, 18.7 mmol) in dimethoxyethane (140 mL) and water (70 mL) was added sodium carbonate (5.15 g, 48.5 mmol), 4-trifluoromethylphenylboronic acid and tetrakis(triphenylphosphine) palladium (0) (0.43 g). The resulting mixture was heated at reflux under nitrogen for 18 h, then allowed to cool to room temperature and the dimethoxyethane removed in vacuo. The residue was diluted with water (30 mL) and extracted CH2Cl2 (2×100 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) eluting 19:1 cyclohexane:EtOAc yielded the title compound as a pale yellow solid (4.47 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under nitrogen for 18 h
  3. customthe dimethoxyethane removed in vacuo
  4. additionThe residue was diluted with water (30 mL)
  5. extractionextracted CH2Cl2 (2×100 mL)
  6. dry with materialThe organic solution was dried (MgSO4)
  7. customthe solvents removed in vacuo
  8. customPurification by Biotage™ chromatography (Silica, 90 g)
  9. washeluting 19:1 cyclohexane

Sources & evidence

ORD record
ord-9d97af0c884f4b7d818c912070e2bdbe
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07199239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes