2-Phenyl-5-tributylstannanyl-pyridine → 4-(6-((4-(Methylsulfonyl)piperazin-1-yl)methyl)-2-(6-phenylpyridin-3-yl)thieno[2,3-d]pyrimidin-4-yl)morpholine

HRID 391102노트

반응식

HRID 391102 반응식
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[S:28][C:15]3[N:16]=[C:17](SC)[N:18]=[C:19]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:14]=3[CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[C:29]1([C:35]2[CH:40]=[CH:39][C:38]([Sn](CCCC)(CCCC)CCCC)=[CH:37][N:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>COCCOC.C(OCC)(=O)C.CSC.[Cu]Br.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[S:28][C:15]3[N:16]=[C:17]([C:38]4[CH:37]=[N:36][C:35]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:40][CH:39]=4)[N:18]=[C:19]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:14]=3[CH:13]=2)[CH2:7][CH2:6]1)(=[O:3])=[O:4]

참가 물질

7

반응물 2

HCID 146900112-Phenyl-5-tributylstannanyl-pyridineHCID 666175866-(4-Methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[2,3-d]pyrimidine

생성물 1

HCID 249465344-(6-((4-(Methylsulfonyl)piperazin-1-yl)methyl)-2-(6-phenylpyridin-3-yl)thieno[2,3-d]pyrimidin-4-yl)morpholine

시약·촉매·용매 4

HCID 2724234Bromo(thiobis(methane))copper촉매HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-(4-methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[2,3-d]pyrimidine (90 mg) in 1,2-dimethoxyethane (10 mL) was added 2-phenyl-5-tributylstannanyl-pyridine (180 mg) and copper(I)bromide-dimethyl sulfide (84 mg) and the reaction mixture was stirred at room temperature for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (12 mg) was then added and the reaction mixture was heated at reflux for 16 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (20 mL) and washed with water (2×20 mL) and brine (2×20 mL). The organic phase was dried (MgSO4), reduced in vacuo and purified by column chromatography to give 387. NMR: (CDCl3): 2.65-2.69 (4 H, m), 2.82 (3 H, s, Me), 3.28-3.32 (4 H, m), 3.84 (2 H, s, CH2), 3.90-3.93 (4 H, m), 4.00-4.02 (4 H, m), 7.18 (1 H, s, Ar), 7.45-7.53 (3 H, m, Ar), 7.85 (1 H, d, J 8.5, Ar), 8.09-8.12 (2 H, m, Ar), 8.76 (1 H, d, J 8.5, Ar) and 9.72 (1 H, d, J 1.2, Ar). MS: (ESI+): MH+ 551.14

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. temperatureAfter cooling to room temperature
  4. washwashed with water (2×20 mL) and brine (2×20 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-285d2ffa317448dd993dc9651770cb81
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383620B2

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