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

HRID 1467816Notes

Reaction equation

HRID 1467816 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-25c439b9be0e4a27b0b72f79b90e474d
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

Loading…