Trimethylsilyldiazomethane → Methyl 5-bromo-2-tert-butylpyrimidine-4-carboxylate

HRID 1016187Notes

Reaction equation

HRID 1016187 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[C:10]([C:19]([OH:21])=[O:20])=[N:11][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:13][CH:14]=1>C1C=CC=CC=1.CO>[CH3:1][O:20][C:19]([C:10]1[C:9]([Br:8])=[CH:14][N:13]=[C:12]([C:15]([CH3:16])([CH3:17])[CH3:18])[N:11]=1)=[O:21]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 122589145-Bromo-2-(tert-butyl)pyrimidine-4-carboxylic acid

Product 1

HCID 57888835Methyl 5-bromo-2-tert-butylpyrimidine-4-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

A 2.0 M hexanes solution of trimethylsilyldiazomethane (11.8 mL, 23.62 mmol) was added dropwise to a stirring solution of 5-bromo-2-tert-butyl-pyrimidine-4-carboxylic acid (6.12 g, 23.62 mmol) in 9:1 benzene/methanol (100 mL), and the reaction was stirred for 2 days. TLC analysis showed that the reaction was complete, so the mixture was concentrated in-vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with water (3×20 mL), dried over sodium sulfate, then concentrated in-vacuo. Purified over silica gel, eluting with 10% ethyl acetate/hexanes, to yield 5.2 g of a colorless oil as product. MS (ESI+)=273/275, (M+H)+. Yield=81%.

Workup

  1. concentrationwas concentrated in-vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with water (3×20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in-vacuo
  6. customPurified over silica gel
  7. washeluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-cdd254809cdb44eba2a25c51d9baa698
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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