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

HRID 1510407ノート

反応式

HRID 1510407 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5bfcfa1867246baa2e6c0eb6dee801c
出典データセット
uspto-grants-2012_07
特許番号
US08211929B2

反応ノート

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