2,4,6-Trichloropyrimidine → 4-Benzyl-2,6-dichloropyrimidine

HRID 2054608Notes

Reaction equation

HRID 2054608 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH2:10]([Mg]Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([Cl:1])[N:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 773782,4,6-TrichloropyrimidineHCID 178418336HCID 178418336, compound

Product 1

HCID 462230714-Benzyl-2,6-dichloropyrimidineYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1.78 g (9.70 mmoles) of 2,4,6-Trichloro-pyrimidine was dissolved in 10 mls of anhydrous THF and chilled to −78° C. 4.9 mls (9.8 mmoles) of benzyl magnesium chloride (2M in THF) was added dropwise and the solution allowed to warm to ambient temperature. The reaction was stirred for 3 hours, then quenched with 20 mls of water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution, dried over NaSO4 and evaporated under reducd pressure. The crude residue was purified by flash chromatography, using EtOAc/Heptane as the eluent to yield 1.08 g (47%) of 4-benzyl-2,6-dichloro-pyrimidine as a light yellow oil. 1H NMR (CDCl3 03-499-77b)

Workup

  1. temperatureto warm to ambient temperature
  2. customquenched with 20 mls of water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed with saturated NaCl solution
  5. dry with materialdried over NaSO4
  6. customevaporated under reducd pressure
  7. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1da13820a4ce4e078a86c31653139614
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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