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

HRID 634988Notes

Reaction equation

HRID 634988 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[OH-].[Na+].[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 14798Sodium HydroxideHCID 53603492-Amino-6-chloropurine

Product 1

HCID 45786-(Phenylmethoxy)-9H-purin-2-amine

Conditions

Temperature
100 °C

Procedure

To a 500 mL 3 neck round bottom flask equipped with a magnetic stirrer, temperature probe and nitrogen inlet was added 2-amino-6-chloropurine (20 g), sodium hyroxide (28 g) and benzyl alcohol (200 mL). The mixture was stirred for 20 minutes and then heated at 100° C. for 2-3 hours. The reaction mixture was then cooled to room temperature and partitioned between methyl t-butyl ether (300 mL) and water (300 mL). The aqueous layer was separated and the pH was adjusted to 7-8 with 6 M HCl. The resulting solid was filtered, washed with water (50 mL) and dried under vacuum at 50° C. for 20 hours to provide the desired product as a pale yellow solid (24.3 g).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompartitioned between methyl t-butyl ether (300 mL) and water (300 mL)
  3. customThe aqueous layer was separated
  4. filtrationThe resulting solid was filtered
  5. washwashed with water (50 mL)
  6. customdried under vacuum at 50° C. for 20 hours

Sources & evidence

ORD record
ord-8a890804f98b4dab913201802d86eee2
Source dataset
uspto-grants-2001_02
Patent number
US06184376B2

Reaction notes

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