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

HRID 1926871

반응식

HRID 1926871 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.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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
160 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5cdc9941b0684131bd89d6c7c9fe9ad1
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183246B2

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