1,2-Dimethoxyethane → 4-Chloro-6-(2-methoxyphenyl)pyrimidine

HRID 1891013Notes

Reaction equation

HRID 1891013 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.COCCOC.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[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

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 709434,6-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 27339582-Methoxyphenylboronic acid

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4,6-dichloropyrimdine (0.98 g), 2-methoxy-benzeneboronic acid (1.0 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (11) (0.54 g), 1,2-dimethoxyethane (60 ml), sodium hydrogen carbonate (1.1 g) and water (20 ml) were heated together at 85° C. for 16 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and the organic phase separated, dried over magnesium sulphate, filtered, evaporated, then purified by column chromatography (silica gel, ethyl acetate/petroleum ether), to give 4-Chloro-6-(2-methoxy-phenyl)-pyrimidine, 1.18 g

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe organic phase separated
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by column chromatography (silica gel, ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-f5a258e002174a20a54ea6b81005f8e5
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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