Methyl 9-bromononanoate → 6-(N-Allyl-N-cyclohexylamino)-9-(8-methoxycarbonyloctyl)-purine

HRID 1721844Notes

Reaction equation

HRID 1721844 reaction equation
[Na].[CH2:2]([N:5]([C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[NH:14][CH:15]=[N:16]2)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH:3]=[CH2:4].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31]>CC(O)C>[CH2:2]([N:5]([C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[N:14]=[CH:15][N:16]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 554142Methyl 9-bromononanoateHCID 5360545SodiumHCID 13851922HCID 13851922, compound

Product 1

HCID 200299766-(N-Allyl-N-cyclohexylamino)-9-(8-methoxycarbonyloctyl)-purineYield 37%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 0.7 g. (30 mmole) sodium in 100 ml. propan-2-ol are added 7.7 g. (30 mmole) 6-(N-allyl-N-cyclohexylamino)-purine (compound of Example 8 j), the reaction mixture is heated to 40° C. for 10 minutes, 7.5 g. (30 mmole) methyl 9-bromononanoate are added thereto, the reaction mixture is heated under reflux for 16 hours and evaporated and the residue is taken up in water, extracted with dichloromethane, dried and evaporated. After chromatography on silica gel (elution agent: dichloromethane/methanol 95:5 v/v), there are obtained 4.8 g. of the title compound (37% of theory) in the form of an oil.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 hours
  3. customevaporated
  4. extractionextracted with dichloromethane
  5. customdried
  6. customevaporated
  7. customAfter chromatography on silica gel (elution agent: dichloromethane/methanol 95:5 v/v), there are obtained 4.8 g

Sources & evidence

ORD record
ord-96d6df8cdf174eaeb41a244b4d4263ab
Source dataset
uspto-grants-1989_08
Patent number
US04853386

Reaction notes

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