Diisopropylethylamine → 2-{6-(4-Chloro-benzyl)-2-[1-(6-methyl-pyrimidin-4-yl)-piperidin-4-ylamino]-pyrimidin-4-yl}-propan-2-ol

HRID 451415노트

반응식

HRID 451415 반응식
Cl.Cl.[CH3:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]2)[CH:5]=1.C(N(CC)C(C)C)(C)C.Cl[C:27]1[N:32]=[C:31]([C:33]([OH:36])([CH3:35])[CH3:34])[CH:30]=[C:29]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)[N:28]=1>CN1CCCC1=O.O1CCOCC1.O>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([CH2:37][C:29]2[N:28]=[C:27]([NH:16][CH:13]3[CH2:14][CH2:15][N:10]([C:6]4[CH:5]=[C:4]([CH3:3])[N:9]=[CH:8][N:7]=4)[CH2:11][CH2:12]3)[N:32]=[C:31]([C:33]([OH:36])([CH3:35])[CH3:34])[CH:30]=2)=[CH:39][CH:40]=1

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 673421331-(6-Methylpyrimidin-4-yl)piperidin-4-amine dihydrochlorideHCID 866567012-[2-Chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol

생성물 1

HCID 533533392-{6-(4-Chloro-benzyl)-2-[1-(6-methyl-pyrimidin-4-yl)-piperidin-4-ylamino]-pyrimidin-4-yl}-propan-2-ol

시약·촉매·용매 3

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매HCID 312751,4-Dioxane용매

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온도
160 °C

실험 절차

To a solution of 1-(6-methyl-pyrimidin-4-yl)-piperidin-4-ylamine dihydrochloride (53 mg, 0.2 mmol) and N,N-diisopropylethyl amine (120 L, 0.7 mmol) in N-methyl-pyrrolidinone (0.5 mL) was added a solution of 2-[2-chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol (65.4 mg, 0.22 mmol)) in dioxane (1.5 mL). The reaction was heated at 160° C. in a microwave oven for 5 hours. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient from AcOEt to AcOEt/EtOH 9:1 (v/v) as eluent. The title compound was obtained as a white solid (27 mg, 30%).

후처리

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using a gradient from AcOEt to AcOEt/EtOH 9:1 (v/v) as eluent

출처 및 근거

ORD 기록
ord-649f495cb4e046c3b1dc68efbc5e8599
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486967B2

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