Hydrochloric Acid → HCID 86723864, compound

HRID 576764Notes

Reaction equation

HRID 576764 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[C:19](=[O:20])[N:18]([CH2:21][CH2:22][CH3:23])[C:17](=[O:24])[N:16]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=4)[C:15]=3[N:34]=CN(C)C)=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].Cl>C(O)C>[NH2:34][C:15]1[N:16]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)[C:17](=[O:24])[N:18]([CH2:21][CH2:22][CH3:23])[C:19](=[O:20])[C:14]=1[C:13]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[N:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86723865HCID 86723865, compound

Product 1

HCID 86723864HCID 86723864, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N′-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-3-(3-nitrophenyl)-2,6-dioxo-1-propyl-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformimidamide (prepared in Example 29) (11.0 mg) in ethanol (1.0 ml) was added 1N hydrochloric acid (2.0 ml) and the resulting mixture was stirred with heating under reflux for six hours. The reaction mixture was concentrated under reduced pressure, and weakly basified with aqueous sodium hydroxide solution, and thereto was added water and the resulting mixture was extracted with ethyl acetate (10 ml×2). The organic layer was washed with saturated saline (10 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol) to afford 4-[5-[6-amino-1-(3-nitrophenyl)-2,4-dioxo-3-propyl-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (7.0 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for six hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionwas added water
  5. extractionthe resulting mixture was extracted with ethyl acetate (10 ml×2)
  6. washThe organic layer was washed with saturated saline (10 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-975cde0f2bb94412958cfb5f364237b2
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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