Hydrochloric Acid → HCID 67159887, 화합물

HRID 2189121노트

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HRID 2189121 반응식
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:25]([O:29][C:30](=[O:39])[CH2:31][O:32][CH:33]1[CH2:37][CH:36]([OH:38])[CH:35]=[CH:34]1)([CH3:28])([CH3:27])[CH3:26].O.Cl>CN(C=O)C>[C:25]([O:29][C:30](=[O:39])[CH2:31][O:32][C@H:33]1[CH2:37][C@@H:36]([O:38][C:2]2[C:3]3[C:10]([C:11]4[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=4)=[C:9]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:35]=[CH:34]1)([CH3:28])([CH3:26])[CH3:27]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 580168974-Chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidineHCID 76739653HCID 76739653, 화합물

생성물 1

HCID 67159887HCID 67159887, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

Dissolve 390.7 mg (1.17 mmol) of 4-chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine and 250 mg (1.17 mmol) of cis-(+/−)-{[(4-hydroxycyclopent-2-en-1-yl]oxy}acetic acid tert-butyl ester in 0.95 ml of DMF, cool to 0° C. and add 0.58 ml (1.17 mmol) of phosphazene base P2-t-Bu (2 M solution in THF). After the end of the addition, warm the mixture to RT and stir for a further 1 h. Then add the reaction mixture to water, adjust to pH 7 with 1N hydrochloric acid and extract three times with dichloromethane. Combine the organic phases, wash with satd. sodium chloride solution, dry over magnesium sulphate and concentrate under reduced pressure. Isolate the crude product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 20:1→5:1). 510 mg (85.3% of theory) of the target compound are obtained.

후처리

  1. additionAfter the end of the addition
  2. temperaturewarm the mixture to RT
  3. extractionextract three times with dichloromethane
  4. washwash with satd
  5. dry with materialsodium chloride solution, dry over magnesium sulphate
  6. concentrationconcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-b4ea59f54aa8433c96d6fd36f940b1c9
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324222B2

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