Water → 2-Amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine

HRID 614931Notes

Reaction equation

HRID 614931 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10]([Cl:17])[N:9]=1.[C:18]([O:26][CH2:27][CH2:28][O:29][CH2:30]Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[NH2:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH2:30][O:29][CH2:28][CH2:27][O:26][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:10]([Cl:17])[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27245002-(Chloromethoxy)ethyl benzoateHCID 53603492-Amino-6-chloropurine

Product 1

HCID 137857472-Amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purineYield 19.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of potassium carbonate (4.1g) and 2-amino-6-chloropurine (5.0g) in dry dimethylformamide (120ml) was stirred for 20 minutes. 2-Benzoyloxyethoxymethyl-chloride (6.3g) was added and the resulting pink suspension stirred at room temperature for 6 days. The reaction mixture was then poured into a mixture of ice and water (210ml) with vigorous stirring. The aqueous mixture was extracted with chloroform (3 × 200ml), and the chloroform solution obtained was washed with a 5% acetic acid solution and then twice with water. The chloroform solution was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was redissolved in a minimal amount of chloroform and the resulting solution applied to a column containing silica gel (200g) in chloroform. The column was eluted with 2% methanol/98% chloroform and the eluant collected in 30ml cuts. The fractions containing 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (determined by TLC) were combined, evaporated and the residue recrystallized from benzene to give 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (2.0g., m.p. 130°-133.5° C.).

Workup

  1. stirringthe resulting pink suspension stirred at room temperature for 6 days
  2. extractionThe aqueous mixture was extracted with chloroform (3 × 200ml)
  3. customthe chloroform solution obtained
  4. washwas washed with a 5% acetic acid solution
  5. dry with materialThe chloroform solution was dried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. dissolutionThe residue was redissolved in a minimal amount of chloroform
  8. additioncontaining silica gel (200g) in chloroform
  9. washThe column was eluted with 2% methanol/98% chloroform
  10. customthe eluant collected in 30ml cuts
  11. additionThe fractions containing 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (determined by TLC)
  12. customevaporated
  13. customthe residue recrystallized from benzene

Sources & evidence

ORD record
ord-af67ef9636324dacbc0c111e24ed1484
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

Loading…