Dimethylformamide → 7-Benzyl-8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1767452Notes

Reaction equation

HRID 1767452 reaction equation
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH3:12])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.CN(C=O)C.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([N:10]1[C:9]2[C:8](=[O:11])[N:7]([CH3:12])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=[C:2]1[Cl:1])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 106618-Chlorotheophylline

Product 1

HCID 3253727-Benzyl-8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Procedure

8-Chloro-1,3-dimethyl-3,7-dihydro-purine-2,6-dione (2.0 g, 9.3 mmol) was dissolved in DMF (50 ml) K2CO3 (2.57 g, 18.6 mmol) and benzyl bromide (1.75 g, 10.3 mmol) were added and the reaction mixture was stirred for 15 hours at room temperature. The reaction mixture was evaporated in vacuo the residue was dissolved in DCM:H2O (1:1) (100 ml) the water phase was extracted with DCM (50 ml) the combined organic phase was dried with MgSO4 filtered and evaporation gave 4A as a white crystalline compound. Yield: 2.92 g. Mp: 145.7–147.1° C.

Workup

  1. customThe reaction mixture was evaporated in vacuo the residue
  2. dissolutionwas dissolved in DCM:H2O (1:1) (100 ml) the water phase
  3. extractionwas extracted with DCM (50 ml) the combined organic phase
  4. dry with materialwas dried with MgSO4
  5. filtrationfiltered
  6. customevaporation

Sources & evidence

ORD record
ord-ec3b75cead184cf88121546e7eba96ab
Source dataset
uspto-grants-2007_06
Patent number
US07235538B2

Reaction notes

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