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

HRID 2189035ノート

反応式

HRID 2189035 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 58280259trans-3-{[5-(4-Methoxyphenyl)-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

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.

後処理

  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

出典と根拠

ORDレコード
ord-db201ce1d9114c41a247cff20858f3ad
出典データセット
uspto-grants-2012_12
特許番号
US08324222B2

反応ノート

読み込み中…