1,3-Dimethyl-6-[2-(dimethylamino)vinyl]-5-nitrouracil → 1H-Pyrrolo(3,2-d)pyrimidine-2,4(3H,5H)-dione, 1,3-dimethyl-

HRID 1467816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467816
[CH3:1][N:2]1[C:9]([CH:10]=[CH:11]N(C)C)=[C:8]([N+:15]([O-])=O)[C:6](=[O:7])[N:5]([CH3:18])[C:3]1=[O:4]>CO.[Pd]>[CH3:1][N:2]1[C:9]2[CH:10]=[CH:11][NH:15][C:8]=2[C:6](=[O:7])[N:5]([CH3:18])[C:3]1=[O:4]

Komponenten

4

Edukt 1

HCID 10834761,3-Dimethyl-6-[2-(dimethylamino)vinyl]-5-nitrouracil

Produkt 1

HCID 2062491H-Pyrrolo(3,2-d)pyrimidine-2,4(3H,5H)-dione, 1,3-dimethyl-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of Step 2 intermediate (0.40 g, 1.573 mmol) in MeOH (80 mL) was added 10% Pd—C (0.2 g) and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 h. The mixture was filtered through a celite bed and was thoroughly washed with MeOH (50 mL). The filtrate was collected and evaporated and the residue thus obtained was purified by column chromatography to afford 0.120 g of the desired compound as an off-white solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 3.23 (s, 3H), 3.38 (s, 3H), 6.17 (s, 1H), 7.25 (s, 1H), 12.09 (s, 1H); APCI-MS (m/z) 180.28 (M+H)+.

Aufarbeitung

  1. filtrationThe mixture was filtered through a celite bed
  2. washwas thoroughly washed with MeOH (50 mL)
  3. customThe filtrate was collected
  4. customevaporated
  5. customthe residue thus obtained
  6. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-25c439b9be0e4a27b0b72f79b90e474d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000159B2

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