Sodium Hydroxide → HCID 57456936, compound

HRID 44409Notes

Reaction equation

HRID 44409 reaction equation
[C:1]([C:3]1[CH2:7][CH2:6][CH2:5][C:4]=1[NH:8][C:9]([NH:11]C(=O)C1C=CC=CC=1)=[O:10])#[N:2].[OH-].[Na+]>CCO>[NH2:2][C:1]1[C:3]2[CH2:7][CH2:6][CH2:5][C:4]=2[NH:8][C:9](=[O:10])[N:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57456937N-(2-cyanocyclopent-1-enylcarbamoyl)benzamide

Product 1

HCID 57456936HCID 57456936, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(2-cyanocyclopent-1-enylcarbamoyl)benzamide (example 75a) (500 mg, 1.96 mmol) and NaOH (2 N, 2.7 mL) in EtOH (20 mL) was stirred at 100° C. under nitrogen for 2 hours. 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, washed with warm water and then 20% EtOH in water to give the final product 4-amino-6,7-dihydro-1H-cyclopenta[d]pyrimidin-2(5H)-one (200 mg, 68%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ10.57 (brs, 1H), 6.93 (brs, 1H), 6.65 (brs, 1H), 2.56 (t, J=7.2 Hz, 2H), 2.43 (t, J=7.6 Hz, 2H) 1.96-1.89 (m, 2H). MS 152 (MH+).

Workup

  1. filtrationthe clear reaction solution was filtered
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with warm water

Sources & evidence

ORD record
ord-90a5d59391a845c99ab4b5d3eeee055d
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

Loading…