Hydrochloric Acid → 2-Amino-7-benzyl-1,7-dihydro-6H-purin-6-one hydrochloride

HRID 1792043Notes

Reaction equation

HRID 1792043 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@@H]1([N:18]2[C:28]3[N:27]=[C:25]([NH2:26])[NH:24][C:22](=[O:23])[C:21]=3[N:20]=[CH:19]2)O[C@H](CO)[C@@H](O)[C@H]1O.[ClH:29].CO>CS(C)=O>[ClH:29].[NH2:26][C:25]1[NH:24][C:22](=[O:23])[C:21]2[N:20]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:19]=[N:18][C:28]=2[N:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7498Benzyl BromideHCID 135398635Guanosine

Product 1

HCID 1356820512-Amino-7-benzyl-1,7-dihydro-6H-purin-6-one hydrochloride

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Benzyl bromide (100 ml) was added dropwise to a suspension of guanosine (100 g) in dimethyl sulfoxide (500 ml) at room temperature, and the resulting reaction mixture was stirred at room temperature for 4 hours. Then, concentrated hydrochloric acid (250 ml) was added thereto. The reaction mixture was stirred at room temperature for 30 minutes, poured into methanol (3 L), and stirred overnight. Deposited crystals were collected by filtration, washed with methanol, and then dried by ventilation at 60° C. for 24 hours to give 82.5 g of the title compound.

Workup

  1. customthe resulting reaction mixture
  2. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  3. stirringstirred overnight
  4. filtrationDeposited crystals were collected by filtration
  5. washwashed with methanol
  6. customdried by ventilation at 60° C. for 24 hours

Sources & evidence

ORD record
ord-9349fb20892142b98b4f4d5634f3a1bb
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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