Acetonitrile → 4-Chloro-6-(2-methoxyphenyl)pyrimidine

HRID 1020068Notes

Reaction equation

HRID 1020068 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C(#N)C.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(O)=O.[Na+].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:1][C:2]1[CH:7]=[C:6]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH3:9])[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 709434,6-DichloropyrimidineHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 152068354-Chloro-6-(2-methoxyphenyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To a 250 ml round bottomed flask was added 4,6-dichloropyrimidine (2.67 g, 17.95 mmol), 2-methoxyphenyl boronic acid (3.00 g, 19.7 mmol), acetonitrile (50 ml) and sodium carbonate (2.95 g, 26.9 mmol). The mixture was sparged with nitrogen for 15 minutes, Pd(PPh3)4 (0.48 g, 0.41 mmol) was then added, and the resulting yellow mixture was heated under an atmosphere of nitrogen at 80° C. for 48 hours. After cooling, the solution was diluted with aqueous NaHCO3 and extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuum. Purification of the residue by silica gel chromatography (2 to 5% ethyl acetate/hexane) afforded 4-chloro-6-(2-methoxy-phenyl)-pyrimidine as a white solid. Yield: 2.5 g

Workup

  1. customThe mixture was sparged with nitrogen for 15 minutes
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customPurification of the residue by silica gel chromatography (2 to 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6212751626174be8a9a78c90969f7076
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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