Water → Dimethyl 2-(2-amino-6-chloropurin-9-ylmethyl)succinate

HRID 2291840Notes

Reaction equation

HRID 2291840 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:12]([O:21][CH3:22])(=[O:20])[C:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH2:14].[H-].[Na+].O>CN(C)C=O.C(Cl)(Cl)Cl.CO>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:14][CH:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:12]([O:21][CH3:22])=[O:20])=[C:4]([Cl:11])[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69240Dimethyl itaconateHCID 53603492-Amino-6-chloropurine

Product 1

HCID 19027590Dimethyl 2-(2-amino-6-chloropurin-9-ylmethyl)succinateYield 66.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of 2-amino-6-chloropurine (4.07 g, 0.024 mol), dimethyl itaconate (5.00 g, 0.032 mol), and sodium hydride (55% in oil, 0.2 g) in 50 ml of dry dimethylformamide was stirred at room temperature for 3 days. About 50 ml of water was added and the mixture was washed with n-hexane (2×50 ml) and then extracted with 2×50 ml of dichloromethane. The combined CH2Cl2 extracts were washed with 2×20 ml of water, dried with magnesium sulfate, and evaporated in vacuum. Treatment with ether and drying afforded a white crystalline product. Chromatography (silica gel, chloroform+methanol 15+1) yielded 5.54 g (71%) or recrystallization (MeOH-H2O) yielded 5.15 g (66.1%) of dimethyl 2-(2-amino-6-chloropurin-9-ylmethyl)succinate.

Workup

  1. washthe mixture was washed with n-hexane (2×50 ml)
  2. extractionextracted with 2×50 ml of dichloromethane
  3. washThe combined CH2Cl2 extracts were washed with 2×20 ml of water
  4. dry with materialdried with magnesium sulfate
  5. customevaporated in vacuum
  6. dry with materialTreatment with ether and drying
  7. customafforded a white crystalline product
  8. custom5.54 g (71%) or recrystallization (MeOH-H2O)

Sources & evidence

ORD record
ord-e4215f896fb6485bb45b8ef0f60a4c7c
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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