Chloropyrazine → HCID 66339447, compound

HRID 2203308Notes

Reaction equation

HRID 2203308 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[C:12]1[CH:17]=[N:16][CH:15]=[CH:14][N:13]=1.[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH2:19][CH3:20]>C1(C)C=CC=CC=1>[N:13]1[CH:14]=[CH:15][N:16]=[CH:17][C:12]=1[CH:19]([CH3:20])[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 73277ChloropyrazineHCID 88561tert-Butyl propionateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 66339447HCID 66339447, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of NaHMDS (1M in toluene, 349 mL, 349 mmol) was added over 5 minutes to a toluene (200 mL) solution containing chloropyrazine (20 g, 175 mmol) and t-butyl propionate (22.73 g, 175 mmol) cooled to 0° C. The solution was stirred at 0° C. for 2 hours and then at room temperature for 4 hours. The reaction was then quenched with saturated aqueous NH4Cl. The mixture was extracted with ethyl acetate and the organic layer concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. m/z=209.3 (M+H).

Workup

  1. waitat room temperature for 4 hours
  2. customThe reaction was then quenched with saturated aqueous NH4Cl
  3. extractionThe mixture was extracted with ethyl acetate
  4. concentrationthe organic layer concentrated
  5. customThe residue was purified by silica gel chromatography
  6. customto give the indicated product

Sources & evidence

ORD record
ord-cd7a6a87169e4f9c93e26a9342a6d540
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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