Ammonia hydroxide → 4-(4-morpholino-6-((4-N-methylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridin-2-amine

HRID 881447

Reaktionsgleichung

Reaktionsgleichung von HRID 881447
F[C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[C:11]3[S:16][C:15]([CH2:17][N:18]4[CH2:23][CH2:22][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:20][CH2:19]4)=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[NH3:35]>>[O:31]1[CH2:32][CH2:33][N:28]([C:10]2[C:11]3[S:16][C:15]([CH2:17][N:18]4[CH2:23][CH2:22][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:20][CH2:19]4)=[CH:14][C:12]=3[N:13]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH2:35])[CH:7]=3)[N:9]=2)[CH2:29][CH2:30]1

Komponenten

3

Edukt 2

HCID 21862953Ammonia hydroxideHCID 669342352-(2-Fluoro-pyridin-4-yl)-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Produkt 1

HCID 249483554-(4-morpholino-6-((4-N-methylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridin-2-amine

Versuchsvorschrift

2-(2-Fluoro-pyridin-4-yl)-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (107 mg) was heated in ammonia hydroxide (90 ml) in a sealed stainless steel pressurized vessel at 150° C. for 5 days. Extraction into chloroform and purification on silica afforded 314 (57 mg). NMR (CDCl3): 2.67-2.71 (4H, m), 2.81 (3H, s), 3.29-3.33 (4H, m), 3.89 (2H, s), 3.89-3.93 (4H, m), 4.08-4.12 (4H, m), 4.55 (2H, br s), 7.36 (1H, s), 7.54 (1H, s), 7.65 (1H, d, J=5.3), 8.21 (1H, d, J=5.3). MS (ESI+): MH+ 490.16 (74%)

Aufarbeitung

  1. extractionExtraction
  2. custominto chloroform and purification on silica

Quellen und Nachweise

ORD-Eintrag
ord-af7e057fb10d44a6bd19063a26499fab
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993563B2

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