Oxalyl chloride → Methyl 5-bromopyrimidine-4-carboxylate

HRID 2174890Notes

Reaction equation

HRID 2174890 reaction equation
[Br:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[N:6][CH:7]=1.[C:11](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[CH3:11][O:9][C:8]([C:3]1[C:2]([Br:1])=[CH:7][N:6]=[CH:5][N:4]=1)=[O:10]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 213292005-Bromopyrimidine-4-carboxylic acid

Product 1

HCID 45790077Methyl 5-bromopyrimidine-4-carboxylateYield 39%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

5-bromopyrimidine-4-carboxylic acid (prepared according to the procedure described in U.S. Pat. No. 4,110,450) (1.0 eq, 6.14 g, 30.2 mmol) was suspended in CH2Cl2 (100 ml). Oxalylchloride (1.1 eq, 2.9 ml, 33.0 mmol) was added followed by 2 drops of DMF. The mixture was stirred at room temperature overnight and the volatiles were removed in vacuo. The residue was taken in MeOH (50 ml) and heated. After evaporation of MeOH in vacuo the compound was dissolved in CH2Cl2 and poured on a prepacked silica gel column. The material was eluted using 20% Ethyl acetate in hexanes. Evaporation of the solvent provided methyl-5-bromopyrimidine-4-carboxylate as a light orange crystalline solid (2.54 g, 39% yield).

Workup

  1. customthe volatiles were removed in vacuo
  2. temperatureheated
  3. customAfter evaporation of MeOH in vacuo the compound
  4. dissolutionwas dissolved in CH2Cl2
  5. additionpoured on a prepacked silica gel column
  6. washThe material was eluted
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4c08a71fc7e04eca8fa6452c61daa4a1
Source dataset
uspto-grants-2015_06
Patent number
US09062043B2

Reaction notes

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