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

HRID 1681630Notes

Reaction equation

HRID 1681630 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=O)C>[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

After 30 g (163 mmol) of 5,6-diamino-1-propyl2,4-(lH,3H)-pyrimidinedione (Japanese Published Unexamined Patent Application No. 57517/80) was suspended in 600 ml of N,N'-dimethylformamide, 17.7 ml (163 mmol) of cyclopentanecarboxylic acid, 30.0 g (196 mmol) of hydroxybenztriazole and 50.5 g (245 mmol) of dicyclohexylcarbodiimide were added to the suspension. The mixture was stirred at room temperature overnight. After insoluble materials were filtered off, the filtrate was evaporated under reduced pressure. To the residue was added 600 ml of 4 N sodium hydroxide aqueous solution and the solution was refluxed for 10 minutes under heating. After ice cooling, insoluble materials were filtered off and 50 ml of methanol was added. The resulting mixture was neutralized with conc. hydrochloric acid. The precipitates were collected by filtration to afford 28.3 g (yield, 66%) of Compound c as a white powder.

Workup

  1. filtrationAfter insoluble materials were filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. additionTo the residue was added 600 ml of 4 N sodium hydroxide aqueous solution
  4. temperaturethe solution was refluxed for 10 minutes
  5. temperatureunder heating
  6. filtrationAfter ice cooling, insoluble materials were filtered off
  7. addition50 ml of methanol was added
  8. filtrationThe precipitates were collected by filtration
  9. customto afford

Sources & evidence

ORD record
ord-0a3afed02ae445ff8d3e23faded261af
Source dataset
uspto-grants-1992_12
Patent number
US05173492

Reaction notes

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