Water → HCID 69978618, compound

HRID 271270Notes

Reaction equation

HRID 271270 reaction equation
Cl[C:2]1[NH:3][C:4](C2OC=CC=2)=[C:5]2[C:9]([N:10]=1)=[N:8][CH:7]=[N:6]2.[CH3:16][Al](C)C.O.[CH3:21][CH2:22][O:23][C:24]([CH3:26])=O>ClCCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:23]1[CH:24]=[CH:26][CH:21]=[C:22]1[N:3]1[CH:4]=[C:5]2[C:9](=[N:8][CH:7]=[N:6]2)[N:10]=[C:2]1[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 16682925TrimethylaluminumHCID 178478322HCID 178478322, compound

Product 1

HCID 69978618HCID 69978618, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-chloro-6-(2-furyl)-1H-purine (1.1 g, 5.0 mmol) and Pd(PPh3)4 (0.58 g, 0.5 mmol) in 1,2-dichloroethane (50 mL) at room temperature was treated dropwise with trimethylaluminium (3.3 mL, 2.0 M hexane), refluxed for 16 h, treated with water (100 mL) then EtOAc (100 mL), stirred for 60 h and filtered through glass microfibre paper. The organic phase was separated, dried (MgSO4), concentrated in vacuo and the resulting solid recrystallised from 90% ethanol to give the title compound (0.30 g, 30%) as a pale brown solid.

Workup

  1. temperaturerefluxed for 16 h
  2. filtrationfiltered through glass microfibre paper
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customthe resulting solid recrystallised from 90% ethanol

Sources & evidence

ORD record
ord-c0bc24cb8fcf465ba5dae845e294779f
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

Loading…