Sodium Hydroxide → 4-aminopyrido[2,3-d]pyrimidin-2(1H)-one

HRID 44383Notes

Reaction equation

HRID 44383 reaction equation
[C:1]([C:3]1[C:4]([NH:9][C:10]([NH:12]C(=O)C2C=CC=CC=2)=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-].[Na+]>CCO>[NH2:2][C:1]1[C:3]2[CH:8]=[CH:7][CH:6]=[N:5][C:4]=2[NH:9][C:10](=[O:11])[N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57456924N-(3-cyanopyridin-2-ylcarbamoyl)benzamide

Product 1

HCID 1785090164-aminopyrido[2,3-d]pyrimidin-2(1H)-oneYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(3-cyanopyridin-2-ylcarbamoyl)benzamide (example 53a) (360 mg, 1.35 mmol) and NaOH (2 N, 1.85 mL) in EtOH (5 mL) was stirred at 100° C. under nitrogen for half an hour. After cooling to room temperature, the clear reaction solution was filtered and the filtrate was carefully neutralized with 10% AcOH with vigorous stirring at 0° C. The resultant precipitate was collected by filtration, and washed with warm 20% EtOH in water to give the final product 4-aminopyrido[2,3-d]pyrimidin-2(1H)-one (120 mg, 55%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ7.22 (dd, J=4.4 Hz, 4.8 Hz, 1H), 7.29 (dd, J=4.8 Hz, 1H), 8.24 (dd, J=2 Hz, 1.6 Hz, 1H), 8.59 (dd, J=2 Hz, 1.6 Hz, 1H), 8.66-8.71 (m, 2H), 8.70 (d, J=1.2 Hz, 1H). MS 162 (MH+).

Workup

  1. filtrationthe clear reaction solution was filtered
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed
  4. temperaturewith warm 20% EtOH in water

Sources & evidence

ORD record
ord-d0223bd493da46f08e583453a661b405
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

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