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Water → 2-[4-(4-Chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamine

HRID 1805996
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1805996
[N:1]([C:4]1[C:5]2[S:25][CH2:24][CH2:23][C:6]=2[N:7]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[N:9]=1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:8]3[N:9]=[C:4]([NH2:1])[C:5]4[S:25][CH2:24][CH2:23][C:6]=4[N:7]=3)[CH2:15][CH2:14]2)=[CH:21][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 866162804-Azido-2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidine

Produkt 1

HCID 684421912-[4-(4-Chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.820 g (1.76 mmol) of 4-azido-2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidine (IV) is placed in 10 mL of tetrahydrofuran and 3.80 mL (3.80 mmol) of lithium aluminum hydride (1M solution in tetrahydrofuran) is slowly added dropwise. The reaction mixture is stirred for 4 hours at ambient temperature. Then 0.55 mL of 1N sodium hydroxide solution and 0.50 mL of water are added, the mixture is boiled for 0.3 hours, then cooled again. It is filtered, the filtrate is dried and evaporated to dryness. The residue is extracted with ethyl acetate and 1 N hydrochloric acid. The product precipitates out, is suction filtered, then extracted with ethyl acetate and 1 N sodium hydroxide solution. The organic phase is washed with water, dried, and evaporated to dryness. The residue is stirred with petroleum ether. 0.513 g of product V (84%) is obtained as a solid (m.p. 176-178° C.). 1H NMR (400 MHz, DMSO): 7.24 (2H, d); 6.98 (2H, d); 6.30 (2H, s); 3.77-3.68 (4H, m); 3.22 (2H, t); 3.17-3.09 (4H, m); 2.99 (2H, t).

Aufarbeitung

  1. waitthe mixture is boiled for 0.3 hours
  2. temperaturecooled again
  3. filtrationIt is filtered
  4. customthe filtrate is dried
  5. customevaporated to dryness
  6. extractionThe residue is extracted with ethyl acetate and 1 N hydrochloric acid
  7. customThe product precipitates out
  8. filtrationfiltered
  9. extractionextracted with ethyl acetate and 1 N sodium hydroxide solution
  10. washThe organic phase is washed with water
  11. customdried
  12. customevaporated to dryness
  13. stirringThe residue is stirred with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-73e2a8b41b214650a11af5ac21e01558
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354531B2

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