Dicyclohexylcarbodiimide → 8-Cyclopentyl-3-propyl-3,7-dihydro-purine-2,6-dione

HRID 326571Notes

Reaction equation

HRID 326571 reaction equation
[NH2:1][C:2]1[C:3](=[O:13])[NH:4][C:5](=[O:12])[N:6]([CH2:9][CH2:10][CH3:11])[C:7]=1[NH2:8].[CH:14]1([C:19](O)=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH:14]1([C:19]2[NH:1][C:2]3[C:3](=[O:13])[NH:4][C:5](=[O:12])[N:6]([CH2:9][CH2:10][CH3:11])[C:7]=3[N:8]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 18840Cyclopentanecarboxylic acidHCID 106313415,6-Diamino-1-propyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 178418300HCID 178418300, compound

Product 1

HCID 156670908-Cyclopentyl-3-propyl-3,7-dihydro-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5,6-diamino-1-propyl-2,4(1H, 3H)pyrimidinedione (Japanese Published Unexamined Patent Application No. 57517/80) in 600 ml of dimethylformamide were sequentially added 17.7 ml (163 mmol) of cyclopentanecarboxylic acid, 30.0 g (196 mmol) of hydroxybenzotriazole and 50.5 g (245 mmol) of dicyclohexylcarbodiimide. The mixture was stirred at room temperature overnight. Insoluble materials were filtered off and the solvent was evaporated under reduced pressure After 600 ml of 4N aqueous sodium hydroxide solution was added to the residue, the mixture was refluxed for 10 minutes under heating. Under ice cooling, insoluble materials were filtered off and 50 ml of methanol was added to the filtrate. After neutralization with conc. hydrochloric acid, the precipitate was collected by filtration to afford 28.3 g (yield, 66%) of Compound c.

Workup

  1. filtrationInsoluble materials were filtered off
  2. customthe solvent was evaporated under reduced pressure After 600 ml of 4N aqueous sodium hydroxide solution
  3. additionwas added to the residue
  4. temperaturethe mixture was refluxed for 10 minutes
  5. temperatureunder heating
  6. filtrationUnder ice cooling, insoluble materials were filtered off
  7. addition50 ml of methanol was added to the filtrate
  8. filtrationAfter neutralization with conc. hydrochloric acid, the precipitate was collected by filtration
  9. customto afford

Sources & evidence

ORD record
ord-f57ed1ab24b842a098d0dcd895749ed8
Source dataset
uspto-grants-1993_12
Patent number
US05270316

Reaction notes

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