Hydrochloric Acid → 3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}butan-2-ol

HRID 1926913노트

반응식

HRID 1926913 반응식
[OH-].[Na+].[CH3:3][C@@H:4]([OH:8])[C@@H:5]([OH:7])[CH3:6].Cl[C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.Cl>C1(C)C=CC=CC=1.COCCOC.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]2[C:11]3[C:10]([O:7][CH:5]([CH3:6])[CH:4]([OH:8])[CH3:3])=[N:15][CH:14]=[N:13][C:12]=3[O:16][C:17]=2[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:24][CH:23]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 220010Meso-2,3-ButanediolHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

생성물 1

HCID 580169433-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}butan-2-ol

시약·촉매·용매 4

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 1140Toluene용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
70 °C

실험 절차

Add 4.8 ml of 12.5 N sodium hydroxide solution to a mixture of 2.68 g (29.70 mmol) (2R,3S)-butane-2,3-diol in 45 ml toluene, 15 ml 1,2-dimethoxyethane and 15 ml water at 70° C. After adding 0.20 g (0.60 mmol) tetra-n-butylammonium hydrogensulphate and 2.00 g (5.94 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine, stir the reaction mixture for 17 h at 70° C. After cooling to room temperature, adjust to pH 7 with concentrated hydrochloric acid. Extract three times with 100 ml dichloromethane each time. Wash the combined organic extracts with satd. sodium chloride solution, dry over sodium sulphate, filter, and concentrate by vacuum evaporation. Purify the raw product by preparative RP-HPLC (gradient: water/acetonitrile). 1.26 g (54% of theor.) of the desired product is obtained as (R,S/S,R) racemate.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionExtract three times with 100 ml dichloromethane each time
  3. washWash the combined organic extracts with satd
  4. dry with materialsodium chloride solution, dry over sodium sulphate
  5. filtrationfilter
  6. concentrationconcentrate by vacuum evaporation
  7. customPurify the raw product by preparative RP-HPLC (gradient: water/acetonitrile)

출처 및 근거

ORD 기록
ord-32d0a414306343448d7dd9c2334e1938
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183246B2

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