Ethyl diazoacetate → HCID 86732043, compound

HRID 1498784Notes

Reaction equation

HRID 1498784 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[C:12]([CH:14]=[CH2:15])[N:11]=[C:10]([CH2:16][CH3:17])[N:9]=2)[N:3]=1.[N+](=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N-]>C1(C)C=CC=CC=1>[CH2:24]([O:23][C:21]([C@@H:20]1[CH2:15][C@H:14]1[C:12]1[CH:13]=[C:8]([N:4]2[C:5]([CH3:7])=[N:6][C:2]([CH3:1])=[N:3]2)[N:9]=[C:10]([CH2:16][CH3:17])[N:11]=1)=[O:22])[CH3:25]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 86732044HCID 86732044, compound

Product 1

HCID 86732043HCID 86732043, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-ethyl-6-vinylpyrimidine (19-3, 860 mg, 3.75 mmol, 1.0 eq.) in toluene (20 mL) at 120° C. was added ethyl diazoacetate (0.79 mL, 7.50 mmol, 2.0 eq.) dropwise and the resulting mixture was refluxed for 4 hours. Toluene was removed by roto-evaporation and the resulting residue was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes) to afford ethyl-trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-ethylpyrimidin-4-yl)cyclopropanecarboxylate (19-4) as a light yellow solid which was carried forward for next step without further purification. LRMS m/z (M+H) 316 found, 316 required.

Workup

  1. temperaturethe resulting mixture was refluxed for 4 hours
  2. customToluene was removed by roto-evaporation
  3. customthe resulting residue was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6de779d626414edf91bfbc6c94ccee61
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

Loading…