6-(4-Methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine → N-methyl-5-(6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

HRID 391139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391139
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[S:20][C:19]3[C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:17][C:16](SC)=[N:15][C:14]=3[CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[CH3:29][NH:30][C:31]1[N:36]=[CH:35][C:34]([Sn](CCCC)(CCCC)CCCC)=[CH:33][N:32]=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>[CH3:29][NH:30][C:31]1[N:36]=[CH:35][C:34]([C:16]2[N:17]=[C:18]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[C:19]3[S:20][C:12]([CH2:11][N:8]4[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]4)=[CH:13][C:14]=3[N:15]=2)=[CH:33][N:32]=1

Komponenten

7

Edukt 2

HCID 666177186-(4-Methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidineHCID 66933863Methyl-(5-tributylstannyl-pyrimidin-2-yl)-amine

Produkt 1

HCID 24948356N-methyl-5-(6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2724234Bromo(thiobis(methane))copperKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-(4-methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (80 mg) in 1,2-dimethoxyethane (10 mL) was added methyl-(5-tributylstannyl-pyrimidin-2-yl)-amine (143 mg) and copper(I)bromide-dimethyl sulfide (74 mg) and the reaction mixture was stirred at room temperature for 10 minutes. Tetrakis(triphenylphosphine)palladium (0) (10 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 417. NMR: (CDCl3): 2.59-2.61 (4 H, m), 2.73 (3 H, s, Me), 3.01 (3 H, d, J 5.1, Me), 3.21-3.24 (4 H, m), 3.78-3.81 (6 H, m), 3.93-3.96 (4 H, m), 7.22 (1 H, s, Ar) and 9.21 (2 H, s, Ar) MS: (ESI+): MH+=505.20

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ad9d7b1494ae4ce58e0534bc656f8281
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383620B2

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