Water → HCID 19043035, 화합물

HRID 483803

반응식

HRID 483803 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 19043035HCID 19043035, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d1218f6eacb444768780ec2eb689daa7
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05227393

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