Phosphorus oxychloride → 3-Benzyl-5-chloro-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 1260437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260437
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15](O)=[C:16]([CH3:21])[C:17](=[O:20])[N:18]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:25]>>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([Cl:25])=[C:16]([CH3:21])[C:17](=[O:20])[N:18]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 598230503-Benzyl-5-hydroxy-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Produkt 1

HCID 598230643-Benzyl-5-chloro-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Versuchsvorschrift

3-Benzyl-5-hydroxy-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (5.5 g, 18.5 mmol) was dissolved in excess POCl3 (50 mL) and heated at reflux for 1 hour. POCl3 was removed in vacuo and the residue dissolved in DCM then quickly washed with saturated sodium bicarbonate solution until neutral pH was observed. The organic layer was dried over MgSO4 and evaporated to dryness to give 7.3 g of the title compound as an impure reddish brown solid. [M+H] calc'd for C16H14ClN3O2, 315. found, 315.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customPOCl3 was removed in vacuo
  4. dissolutionthe residue dissolved in DCM
  5. washthen quickly washed with saturated sodium bicarbonate solution until neutral pH
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e917a769d1d64098acf5fe205234138c
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470837B2

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