Potassium Hydroxide → 6-Amino-1-(4-chloro-benzyl)-1H-pyrimidine-2,4-dione

HRID 2305378Notes

Reaction equation

HRID 2305378 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C:8]([NH:10][C:11](=[O:15])[CH2:12][C:13]#[N:14])=[O:9])=[CH:4][CH:3]=1.[OH-].[K+]>CC(O)C>[NH2:14][C:13]1[N:7]([CH2:6][C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:8](=[O:9])[NH:10][C:11](=[O:15])[CH:12]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18432836HCID 18432836, compound

Product 1

HCID 15266206-Amino-1-(4-chloro-benzyl)-1H-pyrimidine-2,4-dioneYield 98.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

155.6 g of 1-(4-chlorobenzyl)-3-cyanoacetyl-urea in 230 ml of 2-propanol were added to a solution of 14.0 g of KOH in 450 ml of 2-propanol and heated under reflux for 1 hour. After cooling the solid was collected and washed to give the title compound (153.4 g) as a white solid mp 238-41° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling the solid
  4. customwas collected
  5. washwashed

Sources & evidence

ORD record
ord-db6ebdaf8ab44bb090203e6b7832903b
Source dataset
uspto-grants-2002_08
Patent number
US06440979B1

Reaction notes

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