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

HRID 1069391Notes

Reaction equation

HRID 1069391 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([C@@]1(O)[C@@H](CO)O[C@@](C(=O)C)([N:19]2[C:29]3[N:28]=[C:26]([NH2:27])[NH:25][C:23](=[O:24])[C:22]=3[N:21]=[CH:20]2)[C@]1(C(=O)C)O)(=O)C.Cl>C(#N)C>[CH2:1]([N:21]1[C:22]2[C:23](=[O:24])[NH:25][C:26]([NH2:27])=[N:28][C:29]=2[N:19]=[CH:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 1372246632-amino-9-[(2S,3R,4R,5R)-2,3,4-triacetyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one

Product 1

HCID 1354077032-Amino-7-benzyl-1H-purin-6(7H)-oneYield 78.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Eight milliliters of acetonitrile and 2.13 ml (10 equivalents) of benzyl chloride were added to 0.758 g (1.85 mmols) of triacetylguanosine, and the mixture was reacted at 70° C. for 47 hours. The temperature was returned to room temperature, and 3.13 ml (20 equivalents) of conc. hydrochloric acid were added thereto. The reaction was conducted for 4 hours. After 2 hours of the reaction, the solid was precipitated. Ten grams of methanol were added thereto, and the slurry was stirred overnight, and then filtered. The crystals were washed twice with 5 ml of methanol, and dried at 50° C. under reduced pressure to give 0.456 g of 7-benzylguanine crystals in a yield of 78.5%.

Workup

  1. customthe mixture was reacted at 70° C. for 47 hours
  2. customwas returned to room temperature
  3. customAfter 2 hours of the reaction
  4. customthe solid was precipitated
  5. additionTen grams of methanol were added
  6. filtrationfiltered
  7. washThe crystals were washed twice with 5 ml of methanol
  8. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-55f220a8f3da4533b08b6cdbf99b35bd
Source dataset
uspto-grants-2001_06
Patent number
US06252075B1

Reaction notes

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