Tetrahydrofuran → HCID 11300581, compound

HRID 983395Notes

Reaction equation

HRID 983395 reaction equation
[Cl:1][C:2]1[C:16]([F:17])=[CH:15][N:5]2[C:6](=[O:14])[NH:7][C:8](=[O:13])[C:9]([CH:10]3[CH2:12][CH2:11]3)=[C:4]2[C:3]=1[CH3:18].O1CCCC1.[H-].[Na+].[N+:26](C1C=C([N+]([O-])=O)C=CC=1NO)([O-])=O>CN(C)C=O>[NH2:26][N:7]1[C:8](=[O:13])[C:9]([CH:10]2[CH2:12][CH2:11]2)=[C:4]2[C:3]([CH3:18])=[C:2]([Cl:1])[C:16]([F:17])=[CH:15][N:5]2[C:6]1=[O:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5743493N-Hydroxy-2,4-dinitrobenzenamineHCID 9943313HCID 9943313, compound

Product 1

HCID 11300581HCID 11300581, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 5° C. solution of 6-chloro-4-cyclopropyl-7-fluoro-5-methyl-pyrido[1,2-c]pyrimidine-1,3-dione (0.76 g, 2.8 mmol (Example 2)) in a mixture of dry tetrahydrofuran (20 mL) and dry dimethylformamide (10 mL) was added sodium hydride (0.12 g, 3.0 mmol, 60% mineral dispersion) portionwise. After stirring at room temperature for 30 minutes, 2,4-dinitrophenylhydroxylamine (0.65 g, 3.00 mmol) was added. The mixture was then heated at 80° C. for 45 minutes, cooled to ambient temperature, poured into ice water, and extracted with dichloromethane. The combined extracts were washed with brine, dried with sodium sulfate and concentrated. The residue was purified by column chromatography (9:1 ethyl acetate/hexanes) to afford the title compound (0.635 g). MSCI: m/z=284 (MH+).

Workup

  1. temperatureThe mixture was then heated at 80° C. for 45 minutes
  2. temperaturecooled to ambient temperature
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (9:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7c4d43235dde4c96827082c9e9222b2e
Source dataset
uspto-grants-2005_03
Patent number
US06864259B2

Reaction notes

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