Diisopropylethylamine → Methyl 6-[(6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoate

HRID 1926871

反応式

HRID 1926871 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.Cl.[CH3:27][O:28][C:29](=[O:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35]>CN(C=O)C>[CH3:27][O:28][C:29](=[O:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][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

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 579464884-Chloro-6-phenylfuro[2,3-d]pyrimidine

生成物 1

HCID 25123737Methyl 6-[(6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

Heat 2.0 g (8.67 mmol) 4-chloro-6-phenylfuro[2,3-d]pyrimidine and 6.04 ml (34.7 mmol) DIEA in 5 ml DMF to 160° C. Add 3.15 g (17.34 mmol) 6-aminohexanoic acid methyl ester hydrochloride and stir for 4 h at 160° C. After cooling, add the mixture to ice water and extract three times with ethyl acetate. Combine the organic phases and wash with saturated ammonium chloride solution, dry over magnesium sulphate and concentrate under vacuum. Add methanol to the oil residue. Filter off the precipitated solid with suction, wash with methanol again and dry the solid at high vacuum. 1.85 g (57.2% of theor.) of the target compound is obtained.

後処理

  1. temperatureAfter cooling
  2. extractionextract three times with ethyl acetate
  3. washwash with saturated ammonium chloride solution
  4. dry with materialdry over magnesium sulphate
  5. concentrationconcentrate under vacuum
  6. filtrationFilter off the precipitated solid with suction
  7. washwash with methanol again
  8. customdry the solid at high vacuum
  9. custom1.85 g (57.2% of theor.) of the target compound is obtained

出典と根拠

ORDレコード
ord-5cdc9941b0684131bd89d6c7c9fe9ad1
出典データセット
uspto-grants-2012_05
特許番号
US08183246B2

関連ノート

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