Oxalyl chloride → Methyl 5-bromopyrimidine-4-carboxylate

HRID 604353노트

반응식

HRID 604353 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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). LCMS (ES): 95% pure, m/z 217 [M]+; 219 [M+2]+; 1H NMR (CDCl3, 400 MHz) δ 4.04 (s, 3H), 9.02 (s, 1H), 9.21 (s, 1H) ppm.

후처리

  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

출처 및 근거

ORD 기록
ord-89fd55d6d0164a549434408a8c0c9bff
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910600B2

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