Diisopropylethylamine → 2-Phenylpyrimidine-4-carboxylic acid

HRID 1416379노트

반응식

HRID 1416379 반응식
Br[C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C>C(O)C.[Pd]>[C:8]1([C:5]2[N:4]=[C:3]([C:14]([OH:16])=[O:15])[CH:2]=[CH:7][N:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

5

반응물 2

HCID 81531DiisopropylethylamineHCID 185215975-Bromo-2-phenylpyrimidine-4-carboxylic acid

생성물 1

HCID 217091412-Phenylpyrimidine-4-carboxylic acid수율 83.6%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of 500 mg 5-bromo-2-phenyl-4-pyrimidinecarboxylic acid and 1 mL N,N-diisopropylethylamine in 5 mL of ethanol was hydrogenated at 40 psi of H2 for 16 hr using 200 mg of 10% palladium-on-carbon as catalyst. The catalyst was filtered off and the ethanol removed by evaporation under reduced pressure. The residue was dissolved in water, acidified with 3N hydrochloric acid and the precipitate was collected by filtration. This material was air dried to yield 300 mg of 2-phenyl-4-pyrimidinecarboxylic acid as a white solid which was used in the next step without further purification or characterization. A solution of 150 mg of 2-phenyl-4-pyrimidinecarboxylic acid in 1 mL of thionyl chloride was heated at 70° C. for 1 hr, cooled to room temperature and the excess thionyl chloride removed by evaporation under reduced pressure to yield 145 mg of 2-phenyl-4-pyrimidinecarboxylic acid chloride which was used in the next step without further purification or characterization.

후처리

  1. filtrationThe catalyst was filtered off
  2. customthe ethanol removed by evaporation under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. filtrationthe precipitate was collected by filtration
  5. customdried

출처 및 근거

ORD 기록
ord-c69301e068d84f66b2dbea4eb089ff14
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912350

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