4-Nitrophenol → 4-Chloro-6-(4-nitrophenoxy)pyrimidin-2-amine

HRID 387986Notes

Reaction equation

HRID 387986 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:8][C:6]1[CH:5]=[C:4]([O:19][C:16]2[CH:17]=[CH:18][C:13]([N+:10]([O-:12])=[O:11])=[CH:14][CH:15]=2)[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 6766744-Chloro-6-(4-nitrophenoxy)pyrimidin-2-amineYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Amino-4,6-dichloropyrimidine (3.28 g, 20.0 mmol), 4-nitrophenol (2.78 g, 20.0 mmol), and potassium carbonate (4.15 g, 30.0 mmol) were heated and stirred in dimethylformamide (20 ml) at 100° C. for 3 hours. After returning the reaction solution to room temperature, it was poured into ice water (100 ml) and the precipitated crystals were filtered out, washed with water and blow-dried to obtain the title compound (4.93 g, 18.5 mmol, 92%) as colorless crystals.

Workup

  1. customto room temperature
  2. filtrationthe precipitated crystals were filtered out
  3. washwashed with water
  4. customblow-dried

Sources & evidence

ORD record
ord-752e28b9ca0440c8b84699280feda607
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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