p-Toluenesulfonic acid → HCID 86637353, compound

HRID 2189343Notes

Reaction equation

HRID 2189343 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7](=O)[N:8]2[CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:4][N:3]=1.C(OCC)(OCC)OCC.CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 58015786HCID 58015786, compound

Product 1

HCID 86637353HCID 86637353, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-9-(1-ethyl-propyl)-7,9-dihydro-purin-8-one (0.5 g, 2.3 mmol) in DMF (5 mL) is added triethyl orthoformate (3.8 mL, 23 mmol) and TsOH (0.88 g, 2.6 mmol). The reaction is stirred overnight. The reaction mixture is quenched with ice water and extracted with EtOAc. The extracts are dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (SiO2, EtOAC/Hexane 1:3) gives 0.39 g of 2-chloro-9-(1-ethyl-propyl)-9H-purine.

Workup

  1. customThe reaction mixture is quenched with ice water
  2. extractionextracted with EtOAc
  3. dry with materialThe extracts are dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (SiO2, EtOAC/Hexane 1:3)

Sources & evidence

ORD record
ord-85f37e49c5f14ebdb3ba274ef29afb77
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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