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

HRID 1095474

Reaktionsgleichung

Reaktionsgleichung von HRID 1095474
[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 4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine (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-38c2c6bee409438a983fc8b47af8e9e3
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138194B2

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