Ammonium Chloride → 1H-Purine, 6-methyl-

HRID 722083Notes

Reaction equation

HRID 722083 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[CH3:11][Al](C)C.[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1.C1(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)C=CC=CC=1>[CH3:11][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 53592776-ChloropurineHCID 16682925Trimethylaluminum

Product 1

HCID 52875471H-Purine, 6-methyl-

Reagents, catalysts & solvents 3

HCID 178420554HCID 178420554, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 6-chloropurine (0.2 mmol) and tetrakis(triphenylphosphino)-palladium (0.02 mmol) in dry THF (3 mL) was treated with trimethylaluminum (2M in toluene, 0.45 mmol) under nitrogen. The resulting solution was heated to reflux for 3 h, cooled to r.t., diluted with toluene (5 mL), and quenched with methanol (0.5 mL) followed by ammonium chloride (1 mmol). The mixture was heated to reflux for 2 h and filtered while hot through a Celite plug. Evaporation and purification by prep TLC afforded the 6-methylpurine. See J. Med. Chem. 1999, 42, 2064–2086.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 3 h
  3. customquenched with methanol (0.5 mL)
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 2 h
  6. filtrationfiltered while hot through a Celite plug
  7. customEvaporation and purification by prep TLC

Sources & evidence

ORD record
ord-cc665f81c1814c16ac745e8c85bdae31
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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