Methyl iodide → 2-[N-Methyl-(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]pyrimidine-5-carboxylic acid

HRID 1097385노트

반응식

HRID 1097385 반응식
[H-].[Na+].[CH:3]1[C:14]2=[C:15]3[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9][CH2:8][CH2:7][C:6]3=[CH:5][C:4]=1[NH:16][C:17]1[N:22]=[CH:21][C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][N:18]=1.I[CH3:29].[Cl-].[NH4+]>CN(C)C=O>[CH3:29][N:16]([C:4]1[CH:3]=[C:14]2[C:15]3[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9][CH2:8][CH2:7][C:6]=3[CH:5]=1)[C:17]1[N:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:18]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66811056HCID 66811056, 화합물

생성물 1

HCID 585265522-[N-Methyl-(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]pyrimidine-5-carboxylic acid수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A suspension of sodium hydride (60%, 0.008 g) in N,N-dimethylformamide (2 ml) was added with ethyl 2-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]pyrimidine-5-carboxylate (0.032 g) dissolved in N,N-dimethylformamide (1 ml), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was added with iodomethane (0.015 ml), and the mixture was stirred overnight. The reaction mixture was added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, the resulting residue was suspended in ethanol (5 ml), the suspension was added with 20% aqueous sodium hydroxide (1 ml), and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was left to cool and then made acidic with 2 N aqueous hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from ethanol to obtain the title compound (0.027 g, yield: 87%) as colorless needles (melting point: 255-256° C.).

후처리

  1. stirringthe mixture was stirred overnight
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. additionthe suspension was added with 20% aqueous sodium hydroxide (1 ml)
  7. stirringthe mixture was stirred at 50° C. for 3 hours
  8. waitThe reaction mixture was left
  9. temperatureto cool
  10. extractionthe mixture was extracted with chloroform
  11. washThe organic layer was washed successively with water and saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationThe organic layer was concentrated under reduced pressure
  14. customthe resulting residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-91bb8c3c5c5448a8a8f581b7ed879e14
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143260B2

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