Propylene Oxide → 6-(N-Allyl-N-cyclohexylamino)-9-(2-hydroxypropyl)-purine

HRID 1721846Notes

Reaction equation

HRID 1721846 reaction equation
[CH2:1]([N:4]([C:11]1[N:19]=[CH:18][N:17]=[C:16]2[C:12]=1[NH:13][CH:14]=[N:15]2)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[O:26]1[CH:28]([CH3:29])[CH2:27]1>CS(C)=O>[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[CH2:27][CH:28]([OH:26])[CH3:29])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 11430Potassium CarbonateHCID 138519226-(N-allyl-N-cyclohexylamino)-purine

Product 1

HCID 138519426-(N-Allyl-N-cyclohexylamino)-9-(2-hydroxypropyl)-purine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 12.8 g. (50 mmole) 6-[N-allyl-N-cyclohexylamino)-purine (compound of Example 8 j) in 150 ml. dimethyl sulphoxide are added at 40° C. 7.6 g. potassium carbonate. The reaction mixture is stirred for 10 minutes, cooled to ambient temperature, 5.8 g. 1,2-epoxypropane are added dropwise thereto, the reaction mixture is stirred for 5 days at ambient temperature and evaporated and the residue chromatographed on silica gel (elution agent: dichloromethane/methanol 97:3 v/v). After trituration with diethyl ether, there are isolated 5.7 g. of the title compound )36% of theory); m.p. 108°-110° C.

Workup

  1. stirringthe reaction mixture is stirred for 5 days at ambient temperature
  2. customevaporated
  3. customthe residue chromatographed on silica gel (elution agent: dichloromethane/methanol 97:3 v/v)
  4. customAfter trituration with diethyl ether, there are isolated 5.7 g

Sources & evidence

ORD record
ord-d00e3df6eb6e46ec96c7f651f1ce7158
Source dataset
uspto-grants-1989_08
Patent number
US04853386

Reaction notes

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