Sodium Hydroxide → 6-(N-Allyl-N-cyclohexylamino)-9-(8-carboxyoctyl)-purine

HRID 1721845Notes

Reaction equation

HRID 1721845 reaction equation
[CH2:1]([N:4]([C:11]1[N:19]=[CH:18][N:17]=[C:16]2[C:12]=1[N:13]=[CH:14][N:15]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29])[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:2]=[CH2:3].[OH-].[Na+]>C(O)C>[CH2:1]([N:4]([C:11]1[N:19]=[CH:18][N:17]=[C:16]2[C:12]=1[N:13]=[CH:14][N:15]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 200299766-(N-Allyl-N-cyclohexylamino)-9-(8-methoxycarbonyloctyl)-purine

Product 1

HCID 138519416-(N-Allyl-N-cyclohexylamino)-9-(8-carboxyoctyl)-purineYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.2 g. (7.5 mmole) of the compound of Example 13 are heated under reflux for 5 hours with 50 ml. 5% aqueous sodium hydroxide solution and 40 ml. ethanol. The reaction mixture is evaporated and the residue is taken up in water, washed with diethyl ether and the aqueous phase is adjusted to pH 6, extracted with dichloromethane, dried and evaporated. After trituration of the residue with diethyl ether, there are obtained 2.2 g. of the title compound (71% of theory); m.p. 100°-102° C.

Workup

  1. temperatureunder reflux for 5 hours with 50 ml
  2. customThe reaction mixture is evaporated
  3. washwashed with diethyl ether
  4. extractionextracted with dichloromethane
  5. customdried
  6. customevaporated
  7. customAfter trituration of the residue with diethyl ether, there are obtained 2.2 g

Sources & evidence

ORD record
ord-468c9a33d02847a0883d83e37825a367
Source dataset
uspto-grants-1989_08
Patent number
US04853386

Reaction notes

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