Water → HCID 136312202, compound

HRID 2100497Notes

Reaction equation

HRID 2100497 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[N:5][C:4]2[N:20]=[CH:21][CH:22]=[CH:23][C:3]1=2.O.NN.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C>[NH2:9][CH2:8][C:6]1[NH:7][C:2](=[O:1])[C:3]2[CH:23]=[CH:22][CH:21]=[N:20][C:4]=2[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 136345880HCID 136345880, compound

Product 1

HCID 136312202HCID 136312202, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 2-(4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-ylmethyl)-isoindole-1,3-dione (1.0 g, 3.26 mmol) and hydrazine monohydrate (0.48 ml, 9.79 mmol) in ethanol (90 ml) was stirred at 50° C. for 3 hours. The mixture was cooled to ambient temperature and sodium carbonate (0.38 g, 3.59 mmol) and water (1 ml) were added. The suspension was stirred overnight at ambient temperature. The solid residue was filtered off, triturated with CH2Cl2/MeOH (4/1) under reflux conditions. A white solid was filtered off and triturated with TBME to yield 2-aminomethyl-3H-pyrido[2,3-d]pyrimidin-4-one (0.285 g, 1.62 mmol; 50%), as white solid. MS (m/e): 176.8 [M+H+].

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringThe suspension was stirred overnight at ambient temperature
  3. filtrationThe solid residue was filtered off
  4. customtriturated with CH2Cl2/MeOH (4/1) under reflux conditions
  5. filtrationA white solid was filtered off
  6. customtriturated with TBME

Sources & evidence

ORD record
ord-bda849690c5f4dabb2a065660b65cffa
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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