Hydrochloric Acid → 6H-Purin-6-one, 2-amino-1,7-dihydro-7-(2-propen-1-yl)-

HRID 1943782Notes

Reaction equation

HRID 1943782 reaction equation
[C@@H]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)O[C@H](CO)[C@@H](O)[C@H]1O.[CH2:21](Br)[CH:22]=[CH2:23].Cl.[OH-].[Na+]>CO.CS(C)=O>[NH2:18][C:17]1[NH:16][C:14](=[O:15])[C:13]2[N:12]([CH2:23][CH:22]=[CH2:21])[CH:11]=[N:10][C:20]=2[N:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 135398635Guanosine

Product 1

HCID 1354353176H-Purin-6-one, 2-amino-1,7-dihydro-7-(2-propen-1-yl)-Yield 119%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A mixture of guanosine (20 g, 0.071 mol), allyl bromide (14.7 ml, 0.169 mol) and anhydrous DMSO (100 ml) was stirred at rt, under nitrogen, for 18 hours. Concentrated HCl (50 ml of 37%) was added in one portion and the mixture stirred for 45 minutes then poured into MeOH (600 ml). The methanolic solution was neutralised with 2M NaOH (aq) solution and the resulting white precipitate collected by filtration. The white solid was dried under vacuum at 50° C. for 18 hours to afford the title compound (16 g crude, 119%). m/z 192.2[MH+].

Workup

  1. stirringthe mixture stirred for 45 minutes
  2. filtrationthe resulting white precipitate collected by filtration
  3. customThe white solid was dried under vacuum at 50° C. for 18 hours

Sources & evidence

ORD record
ord-5b89e519fe264707a0944266e591f508
Source dataset
uspto-grants-2013_03
Patent number
US08394808B2

Reaction notes

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