4-Nitrophenol → HCID 58931315, compound

HRID 1433432Notes

Reaction equation

HRID 1433432 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[C:23]1[C:24]2[CH:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[NH:29][C:25]=2[N:26]=[CH:27][N:28]=1>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:23]2[C:24]3[CH:31]=[C:30]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[NH:29][C:25]=3[N:26]=[CH:27][N:28]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 9804-Nitrophenol2×HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 224844424-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 58931315HCID 58931315, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
132.5 °C

Procedure

After adding 123 mg of 4-nitrophenol, 136 mg of potassium carbonate and 1.5 ml of dimethylformamide to 113 mg of the 4-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine described in WO97/02266 and PCT/EP96/02728, and stirring the mixture for 15 hours at 130-135° C., and additional 60 mg of 4-nitrophenol and 75 mg of potassium carbonate were added and the mixture was stirred for 6 hours. After returning the mixture to room temperature, water was added, liquid separation and extraction were performed with an ethyl acetate-tetrahydrofuran mixed solvent, and the solid obtained by concentration to dryness was washed with ether to obtain 112 mg of the title compound.

Workup

  1. stirringthe mixture was stirred for 6 hours
  2. customto room temperature
  3. customliquid separation and extraction
  4. customthe solid obtained by concentration to dryness
  5. washwas washed with ether

Sources & evidence

ORD record
ord-0e02c280c7744de3b3bfac0e45b61b59
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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