Diisopropylethylamine → 2-Phenylpyrimidine-4-carboxylic acid

HRID 234122ノート

反応式

HRID 234122 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 217091412-Phenylpyrimidine-4-carboxylic acid収率 83.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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-4pyrimidinecarboxylic 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.

後処理

  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

出典と根拠

ORDレコード
ord-69bca1fed0ec4036b54bce71d46a2f45
出典データセット
uspto-grants-1997_01
特許番号
US05594141

反応ノート

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