6-Aminohexanenitrile → 8-(3-(5-Cyanopentyl-amino-carbonyl)-cyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione

HRID 1684526Notes

Reaction equation

HRID 1684526 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([CH:16]1[CH2:20][CH2:19][CH:18]([C:21]2[NH:29][C:28]3[C:27](=[O:30])[N:26]([CH2:31][CH2:32][CH3:33])[C:25](=[O:34])[N:24]([CH2:35][CH2:36][CH3:37])[C:23]=3[N:22]=2)[CH2:17]1)(O)=[O:14].[NH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]#[N:45]>ClCCl.O1CCCC1>[C:39]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:13]([CH:16]1[CH2:20][CH2:19][CH:18]([C:21]2[NH:29][C:28]3[C:27](=[O:30])[N:26]([CH2:31][CH2:32][CH3:33])[C:25](=[O:34])[N:24]([CH2:35][CH2:36][CH3:37])[C:23]=3[N:22]=2)[CH2:17]1)=[O:14])#[N:38]

Participants

6

Reactant 3

HCID 170796-AminohexanenitrileHCID 682631,1'-CarbonyldiimidazoleHCID 190398248-(3-Carboxycyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione

Product 1

HCID 190398388-(3-(5-Cyanopentyl-amino-carbonyl)-cyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.3 g (1.9 mmol) of carbonyldiimidazole are added to a suspension of 0.67 g (1.9 mmol) of 8-(3-carboxycyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione in 20 ml of dichloromethane and 1 ml of tetrahydrofuran and the mixture is stirred for 35 minutes at ambient temperature. After the addition of 0.21 g (1.9 mmol) of 6-aminocapronitrile the mixture is stirred for a further 24 hours, acidified and washed with water. The organic phase is concentrated by evaporation, the residue is taken up in 5% sodium bicarbonate solution and this solution is extracted with dichloromethane. After drying and evaporation of the organic extracts the title compound is obtained in the form of crystals which, are purified with a mixture of dichloromethane/methanol in the ratio 95:5. 0.67 g (79.8% of theory) of the title compound are obtained in the form of colourless crystals.

Workup

  1. stirringis stirred for a further 24 hours
  2. washwashed with water
  3. concentrationThe organic phase is concentrated by evaporation
  4. extractionthis solution is extracted with dichloromethane
  5. customAfter drying
  6. customevaporation of the organic extracts the title compound
  7. customis obtained in the form of crystals which
  8. customare purified with a mixture of dichloromethane/methanol in the ratio 95:5

Sources & evidence

ORD record
ord-5a3a1dbde2a94ee6b92d0d5764081195
Source dataset
uspto-grants-1997_06
Patent number
US05641784

Reaction notes

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