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

HRID 2189036ノート

反応式

HRID 2189036 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f9cffe85dc554eb5b173dc332165bd8d
出典データセット
uspto-grants-2012_12
特許番号
US08324222B2

反応ノート

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