6-(4-Methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[2,3-d]pyrimidine → 4-(6-((4-(Methylsulfonyl)piperazin-1-yl)methyl)-2-(5-phenylpyridin-3-yl)thieno[2,3-d]pyrimidin-4-yl)morpholine

HRID 881540ノート

反応式

HRID 881540 の反応式
[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:36]=[N:37][CH:38]=[C:39]([Sn](CCCC)(CCCC)CCCC)[CH:40]=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[CH2:6][CH2:7][N:8]([CH2:11][C:12]2[S:28][C:15]3[N:16]=[C:17]([C:39]4[CH:38]=[N:37][CH:36]=[C:35]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH:40]=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)[CH2:9][CH2:10]1)(=[O:3])=[O:4]

参加物

7

反応物 2

HCID 666175866-(4-Methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[2,3-d]pyrimidineHCID 669338703-Phenyl-5-tributylstannanyl-pyridine

生成物 1

HCID 249459924-(6-((4-(Methylsulfonyl)piperazin-1-yl)methyl)-2-(5-phenylpyridin-3-yl)thieno[2,3-d]pyrimidin-4-yl)morpholine

試薬・触媒・溶媒 4

HCID 2724234Bromo(thiobis(methane))copper触媒HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-(4-methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[2,3-d]pyrimidine (135 mg) in 1,2-dimethoxyethane (10 mL) was added 3-phenyl-5-tributylstannanyl-pyridine (270 mg) and copper(I)bromide-dimethyl sulfide (125 mg) and the reaction mixture was stirred at room temperature for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (18 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 403. NMR: (CDCl3): 3.17 (3H, s, Me), 3.93-3.95 (4H, m), 4.13-4.16 (4H, m), 5.28 (2H, s, NH), 7.83 (1H, t, J 7.0, Ar), 7.92 (1H, s, Ar), 8.26 (2H, td, J 7.7 and 1.5, Ar), 8.53-8.54 (1H, m, Ar) and 9.30 (2H, s, Ar). MS: (ESI+): MH+ 497.08

後処理

  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

出典と根拠

ORDレコード
ord-c4a39e68b6ec4c88942f564181b2fdc1
出典データセット
uspto-grants-2015_03
特許番号
US08993563B2

反応ノート

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