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

HRID 1069388Notes

Reaction equation

HRID 1069388 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-dd0b01218b174c46bb60be805e76d568
Source dataset
uspto-grants-2001_06
Patent number
US06252075B1

Reaction notes

Loading…