Methyl iodide → 2,4-Dichloro-6-ethylpyrimidine

HRID 1822811Notes

Reaction equation

HRID 1822811 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Li+].[CH3:11]C([N-]C(C)C)C.IC>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH2:9][CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 794712,4-Dichloro-6-methylpyrimidineHCID 2724682Lithium diisopropylamide

Product 1

HCID 2460102,4-Dichloro-6-ethylpyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4-dichloro-6-methylpyrimidine (4.0 g) in 90 mL THF was cooled to −78 C and treated dropwise with LDA (2 M, 14.7 mL). After 35 min, iodomethane (1.55 mL) was added and the reaction was stirred for 3 more hours at −78 C. The reaction was allowed to slowly warm to room temperature, then quenched with 0.5 mL of water. The mixture was dissolved in water and extracted with ethyl acetate. Chromatography (30% ethyl acetate in hexanes) provided 1.64 g of 2,4-Dichloro-6-ethylpyrimidine.

Workup

  1. customquenched with 0.5 mL of water
  2. dissolutionThe mixture was dissolved in water
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-1fdfd36980a243d0bd47e40ddf2ec4e1
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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