1,1'-Carbonyldiimidazole → 1-(2-ethoxyethyl)-3-ethyl-1H-pyrazolo[4,3-d]pyrimidine-5,7(4H,6H)-dione

HRID 1896199

Reaction equation

HRID 1896199 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[C:15]([CH2:27][CH3:28])=[N:16][N:17]([CH2:22][CH2:23][O:24][CH2:25][CH3:26])[C:18]=1[C:19]([NH2:21])=[O:20]>C(#N)C>[CH2:25]([O:24][CH2:23][CH2:22][N:17]1[C:18]2[C:19](=[O:20])[NH:21][C:1](=[O:2])[NH:13][C:14]=2[C:15]([CH2:27][CH3:28])=[N:16]1)[CH3:26]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 577445394-amino-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazole-5-carboxamide

Product 1

HCID 566051951-(2-ethoxyethyl)-3-ethyl-1H-pyrazolo[4,3-d]pyrimidine-5,7(4H,6H)-dioneYield 87.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of carbonyldiimidazole (12.3 g, 76.1 mmol) in acetonitrile (123 mL) was warmed to 50° C. The 4-amino-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazole-5-carboxamide prepared in step 3 (13.2 g, 58 mmol) was added to the mixture over a period of one hour and the temperature of the mixture was increased to 75° C. during the addition. The mixture was then cooled and stirred overnight. The mixture was cooled in an ice bath and filtered. The filter cake was rinsed with water and dried to provide 12.8 g of the title compound.

Workup

  1. temperaturethe temperature of the mixture was increased to 75° C. during the addition
  2. temperatureThe mixture was then cooled
  3. temperatureThe mixture was cooled in an ice bath
  4. filtrationfiltered
  5. washThe filter cake was rinsed with water
  6. customdried

Sources & evidence

ORD record
ord-0dcd4fbb7f694b759eb4b342704eb1e1
Source dataset
uspto-grants-2013_08
Patent number
US08518956B2

Linked notes

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