Methanol → AB-323/25048145

HRID 1467831Notes

Reaction equation

HRID 1467831 reaction equation
[N+:1]([C:4]1[C:5](=[O:14])[N:6]([CH3:13])[C:7](=[O:12])[N:8]([CH3:11])[C:9]=1[CH3:10])([O-])=O.CO>[Pd].C1(C)C=CC=CC=1>[NH2:1][C:4]1[C:5](=[O:14])[N:6]([CH3:13])[C:7](=[O:12])[N:8]([CH3:11])[C:9]=1[CH3:10]

Participants

5

Reactant 2

HCID 887MethanolHCID 7503695-Nitro-1,3,6-trimethyluracil

Product 1

HCID 816935AB-323/25048145Yield 120.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

To a stirred suspension of 5-nitro-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione (4.2 g, 20.084 mmol) in 1:1 mixture of methanol and toluene (200 ml) was added 10% Pd—C (1.2 g). The reaction mixture was stirred under hydrogen atmosphere at room temperature overnight. The mixture was then filtered over a celite bed and was thoroughly washed with methanol (200 ml). The filtrate was collected and evaporated to give viscous residue which was then purified by column chromatography to afford 4.1 g of the product as an off-white solid.

Workup

  1. filtrationThe mixture was then filtered over a celite bed
  2. washwas thoroughly washed with methanol (200 ml)
  3. customThe filtrate was collected
  4. customevaporated
  5. customto give viscous residue which
  6. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-c3672729829a4f6fb418ad75ae54003a
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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