Sodium Carbonate → 2-amino-6-(2-furyl)-5-nitropyrimidine-4(1H)-one

HRID 1355844Notes

Reaction equation

HRID 1355844 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4](Cl)[N:3]=1.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([C:14]2[O:13][CH:17]=[CH:16][CH:15]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 1354086932-Amino-6-chloro-5-nitro-3,4-dihydropyrimidin-4-one

Product 1

HCID 1356162012-amino-6-(2-furyl)-5-nitropyrimidine-4(1H)-oneYield 44%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 15.7 g (75.3 mmol) 2-amino-6-chloro-5-nitro-3H-pyrimidin-4-one in 300 ml dioxane and 100 ml water at room temperature were added 8.40 g (75.0 mmol) 2-furylboronic acid, 8.70 g (7.53 mmol) tetrakis(triphenylphosphine)palladium(O) and 150 ml (300 mmol) 2M aqueous sodium carbonate solution. The reaction mixture was heated at reflux for 7 h, then concentrated in vacuo. The residue was resuspended in acetone and the insoluble material collected by filtration. This solid material was then dissolved in 1.21 water and acidified to pH 4-5 with 25% hydrochloric acid. The resulting crystals were collected by filtration and washed with water. After drying in vacuo they were additionally washed with dichloromethane to afford 7.33 g (44%) 2-amino-6-furan-2-yl-5-nitro-3H-pyrimidin-4-one as a yellow crystalline solid. ES-MS m/e (%): 221 ([M—H]−, 100).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 7 h
  3. concentrationconcentrated in vacuo
  4. filtrationthe insoluble material collected by filtration
  5. dissolutionThis solid material was then dissolved in 1.21 water
  6. filtrationThe resulting crystals were collected by filtration
  7. washwashed with water
  8. customAfter drying in vacuo they
  9. washwere additionally washed with dichloromethane

Sources & evidence

ORD record
ord-33746e70d11440b58b5b0f2de52d1957
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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