Hydrochloric Acid → 2-Amino-7-benzyl-1H-purin-6(7H)-one

HRID 2374298Notes

Reaction equation

HRID 2374298 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[N:6]=[CH:7][N:8]([C@H]3C[C@@H](CO)[C@H](O)[C@@H]3O)[C:9]=2[N:10]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.[OH-].[Na+]>CS(C)=O.CO>[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[N:6]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:7]=[N:8][C:9]=2[N:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 135417253Guanine, 9-(2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl)-

Product 1

HCID 1354077032-Amino-7-benzyl-1H-purin-6(7H)-oneYield 93.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A mixture of 2-amino-9-[(1S,2R,3S,4S)-2,3-dihydroxy-4-(hydroxymethyl)-cyclopentyl]-1,9-dihydro-6H-purin-6-one (60.0 g, 0.213 mol) and benzyl bromide (60.9 mL, 0.512 mol) in DMSO (300 mL) was stirred at room temperature for 18 h. Concentrated HCl aqueous solution (150 mL) was added to the reaction mixture and stirring was continued for 45 min. The resulting mixture was poured into MeOH (1800 ml). The solution was neutralized with 2 M NaOH solution. The resulting white precipitate was collected by filtration, washed with water, and dried under vacuum to afford the product (48 g, 93.3%). LCMS calculated for C12H12N5O (M+H): 242.1; found: 242.1.

Workup

  1. stirringstirring
  2. waitwas continued for 45 min
  3. filtrationThe resulting white precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8af4549e71634a9b97e646632fc173f9
Source dataset
uspto-grants-2008_12
Patent number
US07462624B2

Reaction notes

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