2-Amino-4,6-dichloropyrimidine → 6-(2-Amino-6-chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid

HRID 1094500Notes

Reaction equation

HRID 1094500 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[OH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([C:21]([OH:23])=[O:22])=[CH:16][CH:15]=[CH:14]2>CC(C)=O.[OH-].[Na+]>[NH2:1][C:2]1[N:7]=[C:6]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21]([OH:23])=[O:22])=[CH:16][CH:15]=[CH:14]3)[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

5

Reactant 2

HCID 655222-Amino-4,6-dichloropyrimidineHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 866252766-(2-Amino-6-chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
62 °C

Procedure

A suspension of 6.56 g (40 mMol) 2-amino-4,6-dichloropyrimidine and 7.52 g (40 mMol) 6-hydroxy-1-naphthoic acid in 160 ml acetone and 80 ml 1 N aqueous NaOH is heated to 62° C. for 36 h. The mixture is cooled to rt, partially concentrated in vacuo and the residue poured into 1.6 l icewater. Under vigorous stirring, 20 ml 2 N HCl are added dropwise (pH≈4). After stirring the suspension for 30 min, the title compound is filtered off and washed with water; HPLC: tRet=12.8.

Workup

  1. temperatureThe mixture is cooled to rt
  2. concentrationpartially concentrated in vacuo
  3. additionthe residue poured into 1.6 l icewater
  4. additionUnder vigorous stirring, 20 ml 2 N HCl are added dropwise (pH≈4)
  5. filtrationthe title compound is filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-1c0652ad36a14595ab72e683ad50d711
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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