Diisopropylethylamine → 6-Chloro-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(3-phenylisoxazol-5-ylmethyl)-pyrimidine-2,4-diamine

HRID 1514331노트

반응식

HRID 1514331 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[C:4]([Cl:17])[N:3]=1.C(N(C(C)C)CC)(C)C.[C:27]1([C:33]2[CH:37]=[C:36]([CH2:38][NH2:39])[O:35][N:34]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)CCC>[Cl:17][C:4]1[N:3]=[C:2]([NH:39][CH2:38][C:36]2[O:35][N:34]=[C:33]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:37]=2)[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27641651-(3-Phenyl-1,2-oxazol-5-yl)methanamineHCID 219910812,6-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine

생성물 1

HCID 116686486-Chloro-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(3-phenylisoxazol-5-ylmethyl)-pyrimidine-2,4-diamine수율 61%

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
90 °C

실험 절차

To a solution of 2,6-dichloropyrimidin-4-yl-(5-cyclopropyl-1H-pyrazol-3-yl)-amine (19.3 g, 71.7 mmol) in 1-butanol (200 mL) was added diisopropylethylamine (23.7 mL, 143 mmol) and 3-phenylisoxazol-5-ylmethylamine (15.0 g, 86.1 mmol). The mixture was stirred at 90° C. for 30 h, then concentrated on a rotary evaporator. The residue was taken up in 100 mL of methanol and boiled until the volume reached around 50 mL. The solution was allowed to cool to room temperature and then placed in the refrigerator overnight. The solid that formed was collected by filtration, while the filtrate was dissolved in dichloromethane and sonicated. The solid that formed was collected and combined with the first recrystallized crop to give the desired product (17.8 g, 61%) as a white solid.

후처리

  1. concentrationconcentrated on a rotary evaporator
  2. temperatureto cool to room temperature
  3. customplaced in the refrigerator overnight
  4. customThe solid that formed
  5. filtrationwas collected by filtration, while the filtrate
  6. dissolutionwas dissolved in dichloromethane
  7. customsonicated
  8. customThe solid that formed
  9. customwas collected

출처 및 근거

ORD 기록
ord-d1c82fe6cdae4dfeba8479cecf1946aa
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222256B2

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