Dimethylformamide → 4-(3-Nitrophenoxy)-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine

HRID 387743Notes

Reaction equation

HRID 387743 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[C:23]1[C:24]2[C:31]([CH3:32])=[C:30]([CH3:33])[NH:29][C:25]=2[N:26]=[CH:27][N:28]=1>O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:23]1[C:24]2[C:31]([CH3:32])=[C:30]([CH3:33])[NH:29][C:25]=2[N:26]=[CH:27][N:28]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 130411444-chloro-5,6-dimethyl-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 589311454-(3-Nitrophenoxy)-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidineYield 46.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

After adding 3-nitrophenol (243 mg), potassium carbonate (268 mg) and dimethylformamide (2 ml) to the 4-chloro-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine (177 mg) described in Journal of Medicinal Chemistry, 1996, Vol. 39, No. 12, 2285-2292, the mixture was stirred at 120-130° C. for 72 hours. This was returned to room temperature, water was added, extraction was performed with a tetrahydrofuran and ethyl acetate mixed solution, and then the organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated to dryness. The obtained crystals were washed with diethyl ether to obtain the title compound (130 mg).

Workup

  1. customThis was returned to room temperature
  2. extractionextraction
  3. washthe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. washThe obtained crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-63b0879abf924eaabe53a54cd990fcb0
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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