Triethylamine → Methyl 5-bromopyrimidine-2-carboxylate

HRID 1011650

Reaction equation

HRID 1011650 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH3:11]CN(CC)CC.S(Cl)(Cl)(=O)=O>CO>[CH3:11][O:9][C:8]([C:5]1[N:6]=[CH:7][C:2]([Br:1])=[CH:3][N:4]=1)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 164629705-Bromopyrimidine-2-carboxylic acid

Product 1

HCID 45790831Methyl 5-bromopyrimidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-2-pyrimidine carboxylic acid (6 g, 29.6 mmol) in MeOH (300 mL) was added Et3N (5.98 g, 59.2 mmol). The mixture was cooled to 0 degrees Celsius, and sulfonyl chloride (5.3 g, 44.4 mmol) was added dropwise to the solution. After addition, the mixture was stirred at rt for 12 hours. The solvent was removed and the residue was dissolved in ethyl acetate. The organic layer was washed with sodium bicarbonate, brine, and dried with sodium sulfate. The solvent was removed to give the pure product. MS: calc'd 217 (MH+), exp 217 (MH+).

Workup

  1. temperatureThe mixture was cooled to 0 degrees Celsius
  2. additionAfter addition
  3. customThe solvent was removed
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe organic layer was washed with sodium bicarbonate, brine
  6. dry with materialdried with sodium sulfate
  7. customThe solvent was removed
  8. customto give the pure product

Sources & evidence

ORD record
ord-19c777ff27fe4c4f8e4625c32492bb88
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Linked notes

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