Hydrazine hydrate (1:1) → 2-(1-aminoethyl)-6-methyl-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 405991Notes

Reaction equation

HRID 405991 reaction equation
[CH3:1][C:2]1[N:7]2[C:8](=[O:31])[C:9]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:10]([CH:12]([N:14]3C(=O)C4C(=CC=CC=4)C3=O)[CH3:13])[N:11]=[C:6]2[CH:5]=[CH:4][CH:3]=1.O.NN>CCO>[NH2:14][CH:12]([C:10]1[N:11]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]2[C:8](=[O:31])[C:9]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 668313572-(1-(6-methyl-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-2-yl)-ethyl)isoindoline-1,3-dione

Product 1

HCID 668313942-(1-aminoethyl)-6-methyl-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(1-(6-methyl-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-2-yl)-ethyl)isoindoline-1,3-dione (0.30g, 0.73 mmol) and hydrazine monohydrate (0.36 mL, 7.3 mmol) in EtOH (14.7 mL) was stirred at 90° C. for 1 h. The mixture was loaded onto silica gel and purified by MPLC (eluted with a gradient of 0-100% (1:10:90 NH4OH:MeOH:DCM solution) in DCM) to afford 2-(1-aminoethyl)-6-methyl-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one as a light yellow foam. Mass Spectrum (ESI) m/e=280.3 (M+1).

Workup

  1. custompurified by MPLC (
  2. washeluted with a gradient of 0-100% (1:10:90 NH4OH:MeOH:DCM solution) in DCM)

Sources & evidence

ORD record
ord-5ab9553b508a48ca9fd5e59f339b66a0
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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