Water → 4-Benzyl-2-chloro-6-methyl-pyrimidine

HRID 1855375Notes

Reaction equation

HRID 1855375 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12](Cl)[N:11]=[C:10]([Cl:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][Zn]C.C(OCC)(=O)C.O>O1CCCC1.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>[CH2:1]([C:8]1[CH:13]=[C:12]([CH3:16])[N:11]=[C:10]([Cl:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 462230714-Benzyl-2,6-dichloropyrimidineHCID 178477796HCID 178477796, compound

Product 1

HCID 866336184-Benzyl-2-chloro-6-methyl-pyrimidineYield 83%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Benzyl-2,6-dichloro-pyrimidine (2.5 g, 10.5 mmol) was dissolved in tetrahydrofuran (40 mL) under an atmosphere of nitrogen and subsequently treated with dimethylzinc (2M in toluene, 5.76 mL) and tetrakis(triphenylphosphine)palladium(0) (245 mg). After stirring for 18 h at ambient temperature, ethyl acetate and water were added, the phases separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and evaporated under reduced pressure. Column chromatography on silica gel using heptane/ethyl acetate 9:1 v/v) as eluent afforded the title compound (1.89 g, 83%) as colorless oil.

Workup

  1. customthe phases separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cc65dc63b2f9491db13e63ec212cf74f
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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