Benzyl Alcohol → 6-(Phenylmethoxy)-9H-purin-2-amine

HRID 1393615Notes

Reaction equation

HRID 1393615 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[NH2:11][C:12]1[N:20]=[C:19]2[C:15]([NH:16][CH:17]=[N:18]2)=[C:14](Cl)[N:13]=1>C(OC)(C)(C)C>[NH2:11][C:12]1[N:20]=[C:19]2[C:15]([NH:16][CH:17]=[N:18]2)=[C:14]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:13]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 14798Sodium Hydroxide2×HCID 53603492-Amino-6-chloropurine

Product 1

HCID 45786-(Phenylmethoxy)-9H-purin-2-amineYield 92%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
85 °C

Procedure

Benzyl alcohol (37.5 g, 0.347 mol) and sodium hydroxide (2.96 g, 0.074 mol) were mixed and heated, and sodium hydroxide was dissolved. After cooling, 2-amino-6-chloropurine (6.00 g, 0.035 mol) was added, and the reaction was completed by heating and stirring at 80-90° C. for 5 hr. Methyl tert-butyl ether (120 ml) was added to the reaction mixture, and the mixture was extracted twice with 1% aqueous sodium hydroxide solution (70 ml). The obtained aqueous alkali layers were combined, washed with toluene, and after removing toluene, neutralized with 35% hydrochloric acid to pH 6-8. The precipitated crystals were collected by filtration. The obtained crystals were dried under reduced pressure to give 2-amino-6-benzyloxypurine (7.60 g, 0.032 mol, yield 92%) as crude crystals.

Workup

  1. temperatureheated
  2. temperatureAfter cooling
  3. temperatureby heating
  4. extractionthe mixture was extracted twice with 1% aqueous sodium hydroxide solution (70 ml)
  5. washwashed with toluene
  6. customafter removing toluene
  7. filtrationThe precipitated crystals were collected by filtration
  8. customThe obtained crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-e3d0d0b9e5c44006a966ed6407134047
Source dataset
uspto-grants-2008_03
Patent number
US07345170B2

Reaction notes

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