N,N-Diethylaniline → 7-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 8714

Reaktionsgleichung

Reaktionsgleichung von HRID 8714
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](=O)[NH:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:32]>>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([Cl:32])=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 1357235075,6,7,8-Tetrahydro-7-(phenylmethyl)pyrido(3,4-d)pyrimidin-4(3H)-one

Produkt 1

HCID 219588387-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 7-benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one 3a (1.0 g, 4.14 mmol) and N,N-diethylaniline (0.37 g, 2.48 mmol) was slowly added POCl3 (12 mL). The mixture was heated to 80° C. for 20 h. After evaporation of the excess of POCl3, the residue was poured into ice, dichloromethane was added and the mixture was made basic (pH=11) with solid Na2CO3. The product was extracted with dichloromethane, dried, and concentrated. Flash column chromatography with 20% ethyl acetate:hexane gave 0.46 g of 7-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 4a as a yellow oil.

Aufarbeitung

  1. customAfter evaporation of the excess of POCl3
  2. additionthe residue was poured into ice, dichloromethane
  3. additionwas added
  4. extractionThe product was extracted with dichloromethane
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d8649f47a7b846b880d52e1adecdf85c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091200B2

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