Water → (+/-)-cis-3-[(6-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexanol

HRID 2189036노트

반응식

HRID 2189036 반응식
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.[NH2:26][C@H:27]1[CH2:32][CH2:31][CH2:30][C@H:29]([OH:33])[CH2:28]1.O>CN(C=O)C>[C:11]1([C:9]2[O:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:26][C@@H:27]4[CH2:32][CH2:31][CH2:30][C@H:29]([OH:33])[CH2:28]4)[C:3]=3[CH:10]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 117882853-Aminocyclohexanol, (1S,3S)-HCID 579464884-Chloro-6-phenylfuro[2,3-d]pyrimidine

생성물 1

HCID 86653748(+/-)-cis-3-[(6-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexanol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

Heat a mixture of 4.0 g (17.34 mmol) of 4-chloro-6-phenylfuro[2,3-d]pyrimidine, 4.5 ml (26 mmol) of DIEA and 2.8 g of (+/−)-cis/trans-3-aminocyclohexanol (approx. 85% strength, approx. 20.8 mmol; approx. 3:1 cis/trans mixture; prepared according to J. Chem. Soc. Perkin Trans. I, 1994, 537) in 15 ml of DMF is heated to 120° C. overnight. After cooling, add the reaction mixture to water and extract three times with ethyl acetate. Wash the combined organic phases with saturated sodium chloride solution, dry over magnesium sulphate and concentrate under reduced pressure. Repeated stirring of the crude product with a mixture of methyl tert-butyl ether and dichloromethane enriches the product in the mother liquor. After concentrating the mother liquor, filter off the product with suction after crystallization from dichloromethane/methanol (10:1) and dry it under reduced pressure. 1.11 g (20.7% of theory) of the target product are obtained.

후처리

  1. temperatureHeat
  2. temperatureAfter cooling
  3. extractionextract three times with ethyl acetate
  4. washWash the combined organic phases with saturated sodium chloride solution
  5. dry with materialdry over magnesium sulphate
  6. concentrationconcentrate under reduced pressure
  7. concentrationAfter concentrating the mother liquor
  8. filtrationfilter off the product with suction
  9. customafter crystallization from dichloromethane/methanol (10:1)
  10. customdry it under reduced pressure
  11. custom1.11 g (20.7% of theory) of the target product are obtained

출처 및 근거

ORD 기록
ord-f9cffe85dc554eb5b173dc332165bd8d
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324222B2

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