HCID 21876400, compound → HCID 21875606, compound

HRID 724124Notes

Reaction equation

HRID 724124 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([CH:18](C(OCC)=O)C(OCC)=O)[C:12]=2[N+:29]([O-:31])=[O:30])=[CH:6][CH:5]=1>Cl>[CH3:17][C:15]1[N:16]=[C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][OH:1])=[CH:9][CH:8]=2)[C:12]([N+:29]([O-:31])=[O:30])=[C:13]([CH3:18])[N:14]=1

Participants

3

Reactant 1

HCID 21876400HCID 21876400, compound

Product 1

HCID 21875606HCID 21875606, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of diethyl 2-(6-{[4-(2-hydroxyethyl)phenyl]amino}-2-methyl-5-nitro-4-pyrimidinyl)propanedioate (step 2, 2.0 g, 6.48 mmol) in 2N aqueous HCl (15 ml) was heated at reflux temperature for 5 h. After cooling, the reaction was quenched with saturated NaHCO3 aqueous solution (100 ml), and the whole was extracted with ethyl acetate (100 ml×3). The organic layer was washed with brine (50 ml), dried (MgSO4), and concentrated. Purification by flash column chromatography eluting with hexane/ethyl acetate (gradient elution from 1:1 to 0:100) to afford 1.33 g (71%) of the title compound as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 h
  3. temperatureAfter cooling
  4. customthe reaction was quenched with saturated NaHCO3 aqueous solution (100 ml)
  5. extractionthe whole was extracted with ethyl acetate (100 ml×3)
  6. washThe organic layer was washed with brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customPurification by flash column chromatography
  10. washeluting with hexane/ethyl acetate (gradient elution from 1:1 to 0:100)

Sources & evidence

ORD record
ord-cd5a192187644f7881dc181152ee962e
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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