Hydrochloric Acid → 2-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutan-1-ol

HRID 1926912노트

반응식

HRID 1926912 반응식
[OH-].[Na+].[C:3]([CH:7]([CH2:10][OH:11])[CH2:8][OH:9])([CH3:6])([CH3:5])[CH3:4].Cl[C:13]1[C:14]2[C:21]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[CH:24][CH:23]=3)=[C:20]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:19][C:15]=2[N:16]=[CH:17][N:18]=1.Cl>C1(C)C=CC=CC=1.COCCOC.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:28]([C:25]1[CH:24]=[CH:23][C:22]([C:21]2[C:14]3[C:13]([O:9][CH2:8][CH:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH2:10][OH:11])=[N:18][CH:17]=[N:16][C:15]=3[O:19][C:20]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:27][CH:26]=1)[CH3:29]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1002262-Tert-butylpropane-1,3-diolHCID 580168974-Chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine

생성물 1

HCID 580168362-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutan-1-ol

시약·촉매·용매 4

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

반응 조건

온도
70 °C

실험 절차

Add 2.7 ml of 11.25 N sodium hydroxide solution to a solution of 1974 mg (14.93 mmol) 2-tert.-butylpropane-1,3-diol in 25 ml toluene, 8 ml 1,2-dimethoxyethane and 8 ml water at 70° C. After adding 101 mg (0.30 mmol) tetra-n-butylammonium hydrogensulphate and 1000 mg (2.99 mmol) 4-chloro-5-(4-ethylphenyl)-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 with dichloromethane. Wash the organic phase with satd. sodium chloride solution, dry over sodium sulphate, and filter. Concentrate the filtrate by vacuum evaporation. Mix the residue with methanol, filter, and wash with diethyl ether. Purify the filtrate by preparative RP-HPLC (gradient: water/acetonitrile). 275 mg (21% of theor.) of the desired product (racemate) is obtained.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionExtract with dichloromethane
  3. washWash the organic phase with satd
  4. dry with materialsodium chloride solution, dry over sodium sulphate
  5. filtrationfilter
  6. concentrationConcentrate the filtrate
  7. customby vacuum evaporation
  8. additionMix the residue with methanol
  9. filtrationfilter
  10. washwash with diethyl ether
  11. customPurify the filtrate by preparative RP-HPLC (gradient: water/acetonitrile)

출처 및 근거

ORD 기록
ord-ee14d551e0b74745823d189abe2e32c5
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183246B2

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