Hydrochloric Acid → 4-Pyridin-3-yl-2-pyrimidin-2-yl-1,2-dihydro-3H-pyrazol-3-one

HRID 1526082Notes

Reaction equation

HRID 1526082 reaction equation
C(O[C:4](=[O:14])[C:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[CH:6]O)C.[NH:15]([C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[NH2:16].[H-].[Na+].Cl>C(O)C>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:5]2[C:4](=[O:14])[N:15]([C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:16][CH:6]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 3465582-HydrazinylpyrimidineHCID 687080883-Hydroxy-2-pyridin-3-yl-acrylic acid ethyl ester

Product 1

HCID 591869714-Pyridin-3-yl-2-pyrimidin-2-yl-1,2-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

193 mg (1 mmol) of the compound from Example 2A and 116 mg (1.05 mmol) 2-hydrazinopyrimidine are initially introduced into 2 ml anhydrous ethanol under argon and the mixture is stirred at RT for 20 h. 40 mg (1 mmol) sodium hydride suspension (60% strength in paraffin oil) are then added in portions, a significant clouding of the reaction solution developing. The mixture is subsequently stirred at RT for 10 min. 1 ml 1 M hydrochloric acid is then added to the dark reaction mixture, a precipitate separating out. The precipitate is filtered off with suction and the residue is washed with water (2×1 ml) and dried in vacuo. 173 mg (72% of th.) of the title compound are obtained.

Workup

  1. stirringThe mixture is subsequently stirred at RT for 10 min
  2. customa precipitate separating out
  3. filtrationThe precipitate is filtered off with suction
  4. washthe residue is washed with water (2×1 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a569643b987345ad9b1af1406816db07
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

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