Water → HCID 21396261, compound

HRID 1439716Notes

Reaction equation

HRID 1439716 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33]Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:33][O:32][CH2:31][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:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 53603492-Amino-6-chloropurineHCID 21396264HCID 21396264, compound

Product 1

HCID 21396261HCID 21396261, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-6-chloropurine (3.0 g) and anhydrous potassium carbonate (2.44 g) in dry dimethylformamide (50 ml) was stirred at room temperature for several hours. To this mixture was added 5 g of 2-(2-benzoyloxyethoxy)ethoxymethyl chloride. The reaction mixture was stirred at room temperature for 4 days and then poured into ice and water. The resulting mixture was extracted with chloroform (3X) and the chloroform extract washed with 10% aqueous acetic acid, with water and then dried over anhydrous sodium sulfate. The solution was filtered and the chloroform evaporated at room temperature and reduced pressure (initially about 20 mm and finally about 1 mm Hg). The residual yellow oil was applied to a column containing silica gel (200 g) in 1:1 ether:chloroform. The column was eluted with 1:1 ether:chloroform followed by chloroform followed by methanol (5%):chloroform (95%). The desired product, 2-amino-6-chloro-9-[2-(2-benzoyloxyethoxy)ethoxymethyl]purine, was eluted in the methanol: chloroform eluate. The fraction exhibiting a single spot on silica gel thin layer chromatography [mobile phase methanol (2%): chloroform (98%)] were combined and evaporated to give a pale yellow oil which gradually solidified. This was recrystallized from benzene to give 2-amino-6-chloro-9-[2-(2-benzoyloxyethoxy)ethoxymethyl]purine 1.5 g), m.p. 111°-112° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 days
  2. extractionThe resulting mixture was extracted with chloroform (3X)
  3. extractionthe chloroform extract
  4. washwashed with 10% aqueous acetic acid, with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solution was filtered
  7. customthe chloroform evaporated at room temperature
  8. additioncontaining silica gel (200 g) in 1:1 ether
  9. washThe column was eluted with 1:1 ether
  10. washThe desired product, 2-amino-6-chloro-9-[2-(2-benzoyloxyethoxy)ethoxymethyl]purine, was eluted in the methanol
  11. customevaporated
  12. customto give a pale yellow oil which
  13. customThis was recrystallized from benzene

Sources & evidence

ORD record
ord-fcc5efd7c00c481fa498d9a7dcd360bf
Source dataset
uspto-grants-1977_11
Patent number
US04060616

Reaction notes

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