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

HRID 1586253Notes

Reaction equation

HRID 1586253 reaction equation
[CH2:1](Br)[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 7498Benzyl BromideHCID 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 85.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Four milliliters of acetonitrile and 0.59 ml (2.7 equivalents) of benzyl bromide were added to 0.755 g (1.84 mmols) of triacetylguanosine, and the mixture was reacted at 50° C. for 16 hours. Subsequently, 2.5 ml (16.1 equivalents) of conc. hydrochloric acid were added thereto. The reaction was conducted at 50° C. for 50 minutes, and the temperature was then returned to room temperature. Then, the solid was precipitated. Fifteen milliliters of methanol were added thereto, and the slurry was stirred for 1 hour, and then filtered. The crystals were washed twice with 5 ml of methanol, and dried at 50° C. under reduced pressure for 2 hours to give 0.496 g of 7-benzylguanine crystals in a yield of 85.8%.

Workup

  1. customthe mixture was reacted at 50° C. for 16 hours
  2. customwas then returned to room temperature
  3. customThen, the solid was precipitated
  4. additionFifteen milliliters of methanol were added
  5. filtrationfiltered
  6. washThe crystals were washed twice with 5 ml of methanol
  7. customdried at 50° C. under reduced pressure for 2 hours

Sources & evidence

ORD record
ord-365896490cf9418ca61e9cdbafc7a80a
Source dataset
uspto-grants-1999_08
Patent number
US05942617

Reaction notes

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