Water → HCID 19043035、化合物

HRID 483803

反応式

HRID 483803 の反応式
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1.[Br:13][C:14]1[CH:28]=[CH:27][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[O:19])=[CH:16][CH:15]=1.O>CCCCCC.C1COCC1>[Br:13][C:14]1[CH:28]=[CH:27][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)([C:7]2[CH:8]=[N:9][CH:10]=[N:11][CH:12]=2)[OH:19])=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 962WaterHCID 728684,4'-DibromobenzophenoneHCID 783445-BromopyrimidineHCID 178418339Butyllithium

生成物 1

HCID 19043035HCID 19043035、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

A solution of 20 ml of 1.6N n-butyllithium in hexane is added dropwise within 30 minutes, with stirring and with the exclusion of moisture, to a solution, cooled to -75°, of 5.2 g (33 mmol) of 5-bromopyrimidine and 10.7 g (31.2 mmol) of 4,4'-dibromobenzophenone in 130 ml of THF. The reaction mixture is stirred for a further 0.5 hour at -75° and then for 16 hours at room temperature; then, while cooling with ice, it is hydrolysed by adding 20 ml of water. The organic phase is separated and diluted with ethyl acetate. The solution is washed with 2N HCl and a semi-saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated by evaporation. The residue is purified by column chromatography (400 g of silica gel, methylene chloride/ethyl acetate 85:15) and recrystallised from ethyl acetate, m.p. 89°-90°, Rf value=0.11 (silica gel, methylene chloride/ethyl acetate 85:15).

後処理

  1. stirringThe reaction mixture is stirred for a further 0.5 hour at -75°
  2. temperaturethen, while cooling with ice, it
  3. customThe organic phase is separated
  4. additiondiluted with ethyl acetate
  5. washThe solution is washed with 2N HCl
  6. dry with materiala semi-saturated sodium chloride solution, dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe residue is purified by column chromatography (400 g of silica gel, methylene chloride/ethyl acetate 85:15)
  10. customrecrystallised from ethyl acetate, m.p. 89°-90°, Rf value=0.11 (silica gel, methylene chloride/ethyl acetate 85:15)

出典と根拠

ORDレコード
ord-d1218f6eacb444768780ec2eb689daa7
出典データセット
uspto-grants-1993_07
特許番号
US05227393

関連ノート

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