Phosphorus oxychloride → 3-Chloro-8-thia-4,6-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2,4,6-tetraene

HRID 1891025

Reaktionsgleichung

Reaktionsgleichung von HRID 1891025
[N:1]1[C:6]2[S:7][C:8]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[C:5]=2[C:4](=O)[NH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:17].C(=O)(O)[O-].[Na+]>O>[Cl:17][C:4]1[C:5]2[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:8]=3[S:7][C:6]=2[N:1]=[CH:2][N:3]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 986145,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-oneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 6995153-Chloro-8-thia-4,6-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2,4,6-tetraeneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-one (0.8 g) and POCl3 (10 mL) was heated at 55-65° C. for 3 h. Water was then added followed by sodium bicarbonate. The resulting mixture was extracted with ethyl acetate. The organic layer was concentrated and the crude compound was purified by silica gel column chromatography using a mixture of hexanes:ethyl acetate (20:1), to give the title compound (0.52 g, 60%). 1H NMR (300 MHz, CDCl3): δ 8.69 (s, 1H), 3.10-3.07 (m, 2H), 2.88-2.86 (m, 2H), 1.89-1.92 (m, 4H). LC-MS (ESI) m/z 225.3 (M+H).

Aufarbeitung

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe crude compound was purified by silica gel column chromatography
  4. additiona mixture of hexanes:ethyl acetate (20:1)

Quellen und Nachweise

ORD-Eintrag
ord-9787b7ab0295430cbdbb8cfbeb2a57b7
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507502B2

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