Hydrazine hydrate (1:1) → (+/-)9-Amino-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1684897Notes

Reaction equation

HRID 1684897 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][CH2:10][CH:11]([N:12]3C(=O)C4C(=CC=CC=4)C3=O)[C:6]2=[N:5][C:4]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:3]1.O.NN>C(O)C>[NH2:12][CH:11]1[C:6]2=[N:5][C:4]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[CH:3][C:2](=[O:1])[N:7]2[CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67265728(+/-) 2-(4-Oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 67265741(+/-)9-Amino-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-oneYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.2 g (8.59 mmol) of (+/−) 2-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-1H-isoindole-1,3(2H)-dione dissolved in 24 mL of ethanol was added 2.09 mL (43 mmol) of hydrazine hydrate and the resulting mixture was stirred under reflux for 2 hours. The mixture was filtered and the solid obtained was triturated with dichloromethane for 24 h, filtered, and the resulting filtrates were evaporated to dryness. The resulting residue was purified on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 98/2 to 96/4 to give 1.37 g (66%) of the desired compound as a brown powder.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationThe mixture was filtered
  3. customthe solid obtained
  4. customwas triturated with dichloromethane for 24 h
  5. filtrationfiltered
  6. customthe resulting filtrates were evaporated to dryness
  7. customThe resulting residue was purified on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 98/2 to 96/4

Sources & evidence

ORD record
ord-c4107991d1224f0aaac192c5b8865178
Source dataset
uspto-grants-2012_04
Patent number
US08148364B2

Reaction notes

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