Trimethylsilyldiazomethane → Methyl 3-methylpyrazine-2-carboxylate

HRID 1045632Notes

Reaction equation

HRID 1045632 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:11][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO>[CH3:11][O:9][C:8]([C:3]1[C:2]([CH3:1])=[N:7][CH:6]=[CH:5][N:4]=1)=[O:10]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 131534683-Methylpyrazine-2-carboxylic acid

Product 1

HCID 13153469Methyl 3-methylpyrazine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 3-methyl-pyrazine-2-carboxylic acid (4.7 g) in toluene (70 ml) and methanol (30 ml) at ambient temperature was added drop wise (trimethylsilyl)diazomethane (2M in diethyl ether) (26 ml). The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated and purified by passing through a pad of silica and eluting with 30% v/v ethyl acetate in iso-hexane to give 3-methyl-pyrazine-2-carboxylic acid methyl ester (3.10 g). 1H-NMR (400 MHz, CDCl3): 8.63 (d, 1H), 8.53 (d, 1H), 4.02 (s, 3H), 2.87 (s, 3H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified
  3. washeluting with 30% v/v ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-d4336c1fafe141a89386d94d50715fa2
Source dataset
uspto-grants-2013_10
Patent number
US08569301B2

Reaction notes

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