Thionyl Chloride → 6-(Benzyloxy)-4-chloropyrido[3,4-d]pyrimidine

HRID 566390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566390
[CH2:1]([O:8][C:9]1[N:19]=[CH:18][C:12]2[N:13]=[CH:14][N:15]=[C:16](O)[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:19]=[CH:18][C:12]2[N:13]=[CH:14][N:15]=[C:16]([Cl:22])[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 1785180356-phenylmethoxy-1H-pyrido[3,4-d]pyrimidin-4-one

Produkt 1

HCID 227274286-(Benzyloxy)-4-chloropyrido[3,4-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideKatalysator

Versuchsvorschrift

6-Benzyloxy-4-hydroxy-pyrido[3,4-d]pyrimidine (1.033 g, 4.1 mmol) was suspended in thionyl chloride (10 ml) under a nitogen atmosphere. DMF (3 drops) was added and the mixture was heated to reflux with stirring for 5.5 hours to give a dark solution, and then left to stand under nitrogen overnight. The mixture was concentrated in vacuo, azeotroping twice with toluene to remove all traces of thionyl cloride and acidic by-products. The material was further dried for two hours in vacuo to give the title compound as a brown solid, used without further purification; δH [2H6]DMSO 8.77(1H,s), 8.13(1H,s), 7.30-7.52 (6H,m), 5.45 (2H,s).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customto give a dark solution
  4. waitleft
  5. waitto stand under nitrogen overnight
  6. concentrationThe mixture was concentrated in vacuo
  7. customazeotroping twice with toluene
  8. customto remove all traces of thionyl cloride and acidic by-products
  9. customThe material was further dried for two hours in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3a7f5c11d6434fa980d7d4140415ba86
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174889B1

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