Ethyl Acetate → 2-(2-methylpyrimidin-5-yl)-morpholino-6-(4-N-methylsulfonyl(piperazin-1-yl)methyl)thieno[2,3-d]pyrimidine

HRID 881433ノート

反応式

HRID 881433 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]4CCOCC4)[C:14]=3[CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[CH3:29][C:30]1[N:35]=[CH:34][C:33]([Sn](CCCC)(CCCC)CCCC)=[CH:32][N:31]=1.[C:49]([O:52][CH2:53][CH3:54])(=O)[CH3:50]>COCCOC.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>[CH3:29][C:30]1[N:31]=[CH:32][C:33]([CH:53]2[CH2:54][N:18]([C:17]3[N:20]=[CH:19][C:14]4[CH:13]=[C:12]([CH2:11][N:8]5[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][CH2:9]5)[S:28][C:15]=4[N:16]=3)[CH2:50][CH2:49][O:52]2)=[CH:34][N:35]=1

参加物

7

反応物 3

HCID 8857Ethyl AcetateHCID 666175866-(4-Methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[2,3-d]pyrimidineHCID 669338622-Methyl-5-tributylstannanyl-pyrimidine

生成物 1

HCID 669341152-(2-methylpyrimidin-5-yl)-morpholino-6-(4-N-methylsulfonyl(piperazin-1-yl)methyl)thieno[2,3-d]pyrimidine

試薬・触媒・溶媒 3

HCID 2724234Bromo(thiobis(methane))copper触媒HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane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 (104 mg) in 1,2-dimethoxyethane (10 mL) was added 2-methyl-5-tributylstannanyl-pyrimidine (180 mg) (prepared as above) and copper(I)bromide-dimethyl sulfide (96 mg) and the reaction mixture was stirred at room temperature for 10 minutes. Tetrakis(triphenylphosphine)palladium (0) (14 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 304. NMR: (CDCl3) 2.67-2.70 (4H, m), 2.82 (3H, s, Me), 2.84 (3H, s, Me), 3.30-3.32 (4H, m), 3.85 (2H, s, CH2), 3.91-3.92 (4H, m), 3.98-4.01 (4H, m), 7.01 (1H, s, Ar) and 9.58 (2H, s, Ar). MS: (ESI+): MH+=490.14

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-f4cba86d2e204f45b8ec290a978c660b
出典データセット
uspto-grants-2015_03
特許番号
US08993563B2

反応ノート

読み込み中…