4-Nitrophenyl chloroformate → HCID 86586006, compound

HRID 2183555Notes

Reaction equation

HRID 2183555 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:3]=1[C:18]#[N:19].[Li+].CC([N-]C(C)C)C.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:30]>C1COCC1>[N+:38]([C:35]1[CH:34]=[CH:33][C:32]([O:31][C:29]([N:5]2[CH:4]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=3)[C:3]([C:18]#[N:19])=[C:2]([CH3:1])[NH:7][C:6]2=[O:8])=[O:30])=[CH:37][CH:36]=1)([O-:40])=[O:39]

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 2724682Lithium diisopropylamideHCID 22473425HCID 22473425, compound

Product 1

HCID 86586006HCID 86586006, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 6-Methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile (0.43 g, 1.7 mmol, prepared by the method described in Example 26, Step 1, in 77% yield) in THF (15 mL) at −78° C. was added LDA (1.25 mL, 2.5 mmol, 2.0 M in hexanes). The resulting mixture was stirred at −78° C. for 15 min, warmed to −25° C. for 15 min, recooled to −78° C. and 4-nitrophenyl chloroformate (0.50 g, 2.5 mmol) was added in one portion. The reaction mixture was stirred at −78° C. for 15 min, gradually warmed to room temperature, quenched with water and extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using 50% to 70% ethyl acetate-hexane as eluant to give the title compound as a light yellow solid (0.38 g, 53%).

Workup

  1. customprepared by the method
  2. customat −78° C.
  3. temperaturewarmed to −25° C. for 15 min
  4. customrecooled to −78° C.
  5. stirringThe reaction mixture was stirred at −78° C. for 15 min
  6. temperaturegradually warmed to room temperature
  7. customquenched with water
  8. extractionextracted with ethyl acetate
  9. extractionThe organic extract
  10. washwas washed with brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by flash column chromatography on silica gel using 50% to 70% ethyl acetate-hexane as eluant

Sources & evidence

ORD record
ord-c05b7661246f468c9a49bdb26c118396
Source dataset
uspto-grants-2005_05
Patent number
US06900214B2

Reaction notes

Loading…