N-methyl-2-pyrrolidone → 5-[8-(3,3-Dimethylpiperazin-1-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine

HRID 421427노트

반응식

HRID 421427 반응식
CN1CCCC1=O.Cl[C:9]1[N:10]([CH2:31][C:32]([F:35])([F:34])[F:33])[C:11]2[C:16]([N:17]=1)=[C:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:14]=[C:13]([C:24]1[CH:25]=[N:26][C:27]([NH2:30])=[N:28][CH:29]=1)[N:12]=2.[CH3:36][C:37]1([CH3:43])[CH2:42][NH:41][CH2:40][CH2:39][NH:38]1>C(Cl)Cl.CO>[CH3:36][C:37]1([CH3:43])[NH:38][CH2:39][CH2:40][N:41]([C:9]2[N:10]([CH2:31][C:32]([F:34])([F:33])[F:35])[C:11]3[C:16]([N:17]=2)=[C:15]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[N:14]=[C:13]([C:24]2[CH:25]=[N:26][C:27]([NH2:30])=[N:28][CH:29]=2)[N:12]=3)[CH2:42]1

참가 물질

5

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 146641862,2-DimethylpiperazineHCID 593335342-(2-aminopyrimidin-5-yl)-8-chloro-6-(morpholin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purine

생성물 1

HCID 593335975-[8-(3,3-Dimethylpiperazin-1-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine수율 95%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

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온도
120 °C

실험 절차

An N-methyl-2-pyrrolidone suspension (5.0 ml) of 5-[8-chloro-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine (492.8 mg, 1.19 mmol) and 2,2-dimethylpiperazine (JMC, 1995, Vol. 38, No. 22, 4389) (571.3 mg, 4.75 mmol) was heated at 120° C. to dissolve and the resulting mixture was stirred at 100° C. for 12 hours. The resulting mixture was left standing to cool, poured into methylene chloride-methanol (10:1), and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride:methanol=49:1 to 13:1) to give the title compound (554.4 mg, 95%) as a pale yellow solid.

후처리

  1. dissolutionto dissolve
  2. waitThe resulting mixture was left
  3. temperatureto cool
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationthe mixture was filtrated
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride:methanol=49:1 to 13:1)

출처 및 근거

ORD 기록
ord-36e8d6b43a664e378d315382031d98bb
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097622B2

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