Diisopropylethylamine → trans-3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol

HRID 2189035노트

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HRID 2189035 반응식
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O: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.[NH2:25][C@H:26]1[CH2:31][CH2:30][CH2:29][C@H:28]([OH:32])[CH2:27]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:2]([NH:25][C@H:26]4[CH2:31][CH2:30][CH2:29][C@H:28]([OH:32])[CH2:27]4)=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 117882853-Aminocyclohexanol, (1S,3S)-HCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

생성물 1

HCID 58280259trans-3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

Initially charge 1.0 g (2.97 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 513 mg (approx. 4.5 mmol) of (+/−)-cis/trans-3-aminocyclohexanol (approx. 3:1 cis/trans mixture; prepared according to J. Chem: Soc. Perkin Trans. I, 1994, 537) in 2.7 ml of DMF. After adding 1.03 ml (5.94 mmol) of DIEA, heat the mixture to 120° C. for 2 h. After cooling, add to ice-water. Filter off the precipitated solid with suction, wash with water and dry under reduced pressure. Purify the crude product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1→1:2). 1.05 g (85.1% of theory) of the target product are obtained as a cis/trans mixture.

후처리

  1. temperatureAfter cooling
  2. filtrationFilter off the precipitated solid with suction
  3. washwash with water
  4. customdry under reduced pressure
  5. customPurify the crude product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1→1:2)
  6. custom1.05 g (85.1% of theory) of the target product are obtained as a cis/trans mixture

출처 및 근거

ORD 기록
ord-db201ce1d9114c41a247cff20858f3ad
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324222B2

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