Sodium Carbonate → 4-(4-Chlorophenyl)-2-(methylthio)pyrimidine

HRID 1269624Notes

Reaction equation

HRID 1269624 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 971134-Chloro-2-methylthiopyrimidine

Product 1

HCID 28211934-(4-Chlorophenyl)-2-(methylthio)pyrimidineYield 89.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-chloro-2-(methylthio)pyrimidine (3 g, 18.7 mmol), 4-chloro-phenylboronic acid (3.5 g, 22.3 mmol), tetrakis(triphenylphosphine)palladium (0) (0.43 g, 0.37 mmol), sodium carbonate (5.15 g, 48.5 mmol) in 1,2-dimethoxyethane (140 mL) and water (70 mL) was heated at 90° C. for 20 h under nitrogen. The cooled reaction mixture was concentrated In vacuo, diluted with water (50 mL), extracted with CH2Cl2 (2×100 ml), dried (Na2SO4) and the solvent removed in vacuo. Purification by Biotage™ chromatography (silica, 90 g) eluting with 10:1 to 2:1 cyclohexane:EtOAc afforded the title compound as a white solid (3.98 g).

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated In vacuo
  3. additiondiluted with water (50 mL)
  4. extractionextracted with CH2Cl2 (2×100 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customPurification by Biotage™ chromatography (silica, 90 g)
  8. washeluting with 10:1 to 2:1 cyclohexane

Sources & evidence

ORD record
ord-2359907408624418ba48aeac5870abe4
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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