Sodium hydride → 2-(6-(4-(2-Morpholinoethyl)piperazin-1-yl)pyrimidin-4-ylamino)thiazole-5-carbonitrile

HRID 1241369

Reaktionsgleichung

Reaktionsgleichung von HRID 1241369
[N:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=3)[CH2:11][CH2:10]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:25]1[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=1>>[N:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:25]4[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=4)[CH:16]=3)[CH2:11][CH2:10]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 219346006-[4-(2-Morpholin-4-ylethyl)piperazin-1-yl]pyrimidin-4-amine

Produkt 1

HCID 101116132-(6-(4-(2-Morpholinoethyl)piperazin-1-yl)pyrimidin-4-ylamino)thiazole-5-carbonitrile

Versuchsvorschrift

6-[4-(2-morpholin-4-ylethyl)piperazin-1-yl]pyrimidin-4-amine 7-4 (1.5 g, 5.13 mmol), sodium hydride (0.41 g, 10.26 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.74 g, 5.13 mmol) were treated as in Scheme 4 above. The product was purified on a silica column eluted with DCM:MeOH:NH4OH (95:5:0.5 and 9:1:0.1) and isolated directly from the appropriate fractions after they were concentrated and the residue was suspended in methanol and filtered. 1H-NMR (CDCl3): 9.27 ppm (s, 1H); 8.45 ppm (s, 1H); 7.90 ppm (s, 1H); 5.87 ppm (s, 1H); 3.72 ppm (m, 4H); 3.65 ppm (s, 4H); 2.57 ppm (m, 8H); 2.50 ppm (s, 4H).

Aufarbeitung

  1. customThe product was purified on a silica column
  2. washeluted with DCM:MeOH:NH4OH (95:5:0.5 and 9:1:0.1)
  3. customisolated directly from the appropriate fractions after they
  4. concentrationwere concentrated
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-b024a20a82de4e53adb1a9b072bbe885
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115597B2

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