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

HRID 1586254Notes

Reaction equation

HRID 1586254 reaction equation
C([C@@]1(O)[C@@H](CO)O[C@@](C(=O)C)([N:11]2[C:21]3[N:20]=[C:18]([NH2:19])[NH:17][C:15](=[O:16])[C:14]=3[N:13]=[CH:12]2)[C@]1(C(=O)C)O)(=O)C.[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(Cl)C1C=CC=CC=1.Cl>C(#N)C>[CH2:30]([N:13]1[C:14]2[C:15](=[O:16])[NH:17][C:18]([NH2:19])=[N:20][C:21]=2[N:11]=[CH:12]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 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 80.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triacetylguanosine (0.756 g, 1.85 mmols) was suspended in 6 ml of acetonitrile, and 0.28 ml (1.25 equivalents) of benzyl bromide and 0.27 ml (1.25 equivalents) of benzyl chloride were added to the suspension. The mixture was reacted at 50° C. for 24 hours and at 60° for 23 hours. The temperature was returned to room temperature, and 1.58 ml (10.1 equivalents) of conc. hydrochloric acid were added thereto. The resulting mixture was reacted for 3 hours. After 40 minutes of the reaction, the solid was precipitated. Fifteen milliliters of methanol were added thereto, and the slurry was stirred for 1.5 hours, and then filtered. The crystals were washed twice with 5 ml of methanol, and dried at 50° C. under reduced pressure for 4 hours to give 0.468 g of 7-benzylguanine crystals in a yield of 80.5%.

Workup

  1. customThe mixture was reacted at 50° C. for 24 hours and at 60° for 23 hours
  2. customwas returned to room temperature
  3. customThe resulting mixture was reacted for 3 hours
  4. customAfter 40 minutes of the reaction
  5. customthe solid was precipitated
  6. additionFifteen milliliters of methanol were added
  7. filtrationfiltered
  8. washThe crystals were washed twice with 5 ml of methanol
  9. customdried at 50° C. under reduced pressure for 4 hours

Sources & evidence

ORD record
ord-e94a320485fb453cb37b6996b8eba06c
Source dataset
uspto-grants-1999_08
Patent number
US05942617

Reaction notes

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