Ethyl diazoacetate → HCID 86732070, compound

HRID 1498809Notes

Reaction equation

HRID 1498809 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH2:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[N+](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N-]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([CH3:10])[N:5]=[C:6]([CH:8]2[CH2:9][CH:13]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 86732069HCID 86732069, compound

Product 1

HCID 86732070HCID 86732070, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4-chloro-2-methyl-6-vinylpyrimidine (4-1, 15.0 g, 97 mmol 1.0 eq) in Toluene (300 mL) was heated to 100° C. under a nitrogen atmosphere. A solution of ethyl diazoacetate (30.2 mL, 291 mmol, 3.0 eq) was added as a solution in toluene (100 mL) over 1.5 hours. Heating was continued for 2 hours. The reaction mixture was allowed to cool to room temperature and concentrated to dryness. The residue was partitioned between saturated sodium bicarbonate solution (1 L) and ethyl acetate (1 L). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to dryness. The resulting residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes) to give ethyl 2-(6-chloro-2-methylpyrimidin-4-yl)cyclopropanecarboxylate (4-2) as a colorless oil.

Workup

  1. temperatureHeating
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between saturated sodium bicarbonate solution (1 L) and ethyl acetate (1 L)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe resulting residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6fa7c06accc340b19a979dd3cee8283b
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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