4-Benzyl-2,6-dichloropyrimidine → 4-Benzyl-2-chloro-pyrimidine

HRID 1855325Notes

Reaction equation

HRID 1855325 reaction equation
[CH2:1]([C:8]1[N:13]=[C:12]([Cl:14])[N:11]=[C:10](Cl)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N.C(OCC)(=O)C.[Zn]>[CH2:1]([C:8]1[CH:9]=[CH:10][N:11]=[C:12]([Cl:14])[N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 462230714-Benzyl-2,6-dichloropyrimidine

Product 1

HCID 183533314-Benzyl-2-chloro-pyrimidineYield 102.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 222AmmoniaSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To an emulsion of 6-benzyl-2,4-dichloro-pyrimidine (239 mg, 1 mmol) in 25% aqueous ammonia solution (1 mL) was added after stirring for 10 min at 0° C. zinc powder (82 mg, 1.25 mmol). The reaction was stirred at 20° C. for 16 h. The yellow suspension was diluted with ethyl acetate an insoluble material was filtered off. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated under reduced pressure to yield the crude title compound (210 mg, 92%) as a yellow oil.

Workup

  1. filtrationwas filtered off
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c51372fc5ba742a7b6bf8c65b587339b
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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