Triethylamine → HCID 57762608, 화합물

HRID 1360051노트

반응식

HRID 1360051 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.C(N(CC)CC)C>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydrideHCID 22346771HCID 22346771, 화합물

생성물 1

HCID 57762608HCID 57762608, 화합물수율 85%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

Under an argon atmosphere, N-(4-bromophenyl)pyrimidin-2-amine (200 mg) was added to a suspension of sodium hydride (48 mg) in anhydrous DMF (8 ml), and the resulting mixture was stirred at room temperature for 30 minutes. The reaction solution was cooled to 0° C., and 3-chloromethylpyridine hydrochloride (600 mg) and triethylamine (1.00 ml) were added thereto, followed by stirring the resulting mixture at room temperature for 2 hours. Saturated brine was added to the reaction solution and the resulting mixture was extracted 3 times with ethyl acetate. Organic layers were washed 3 times with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent:ethyl acetate/hexane=3/1) to obtain N-(4-bromophenyl)-N-((pyridin-3-yl)methyl)pyrimidin-2-amine (232 mg). NMR (H1, CDCl3): δ 5.23 (2H, s), 6.65 (1H, t, J=4.6 Hz), 7.08-7.12 (2H, m), 7.20 (1H, dd, J=7.8, 4.9 Hz), 7.46-7.50 (2H, m), 7.59-7.61 (1H, m), 8.35 (2H, d, J=4.6 Hz), 8.49 (1H, dd, J=4.9, 1.5 Hz), 8.54 (1H, d, J=2.2 Hz)

후처리

  1. temperatureThe reaction solution was cooled to 0° C.
  2. stirringby stirring the resulting mixture at room temperature for 2 hours
  3. extractionthe resulting mixture was extracted 3 times with ethyl acetate
  4. washOrganic layers were washed 3 times with water
  5. dry with materialonce with saturated brine, and dried over anhydrous sodium sulfate
  6. customAfter removing anhydrous sodium sulfate
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by column chromatography (silica gel, eluent:ethyl acetate/hexane=3/1)

출처 및 근거

ORD 기록
ord-d9c514ffeaf44bb28577e78050988791
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879837B2

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