Triethylamine → 2-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 2189298Notes

Reaction equation

HRID 2189298 reaction equation
[CH2:1]([NH:4][C:5]1[C:10](Br)=[CH:9][N:8]=[C:7]([Cl:12])[N:6]=1)[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:12][C:7]1[N:8]=[CH:9][C:10]2[C:2]([CH3:3])=[CH:1][NH:4][C:5]=2[N:6]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86637340HCID 86637340, compound

Product 1

HCID 707002742-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidineYield 40%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Allyl-(5-bromo-2-chloro-pyrimidin-4-yl)-amine (1 g, 4 mmol), palladium(II) acetate, (90 mg, 0.40 mmol), triphenylphosphine (211 mg, 0.80 mmol) and triethylamine (1.1 mL, 8.0 mmol) in DMF (10 mL) is heated at 100° C. overnight. After cooling to room temperature the reaction mixture is diluted with ethyl acetate and washed with brine. The organic phase is dried (anhydrous Na2SO4) and the solvent is evaporated. The crude product is purified by flash chromatography (gradient elution EtOAC:Heptanes 0:0 to 1:1) on silicagel to afford 2-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine as a white solid (40%).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. washwashed with brine
  3. dry with materialThe organic phase is dried (anhydrous Na2SO4)
  4. customthe solvent is evaporated
  5. customThe crude product is purified by flash chromatography (gradient elution EtOAC:Heptanes 0:0 to 1:1) on silicagel

Sources & evidence

ORD record
ord-19d087b7a9f74f90a457138287b6f9c2
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

Loading…