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

HRID 1094501Notes

Reaction equation

HRID 1094501 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:5]=[C:4](Cl)[N:3]=1>C1COCC1.CCN(CC)CC.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 1

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

Product 1

HCID 574551596-(2-Amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

24.4 g (77.5 mMol) 6-(2-amino-6-chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid in 3.5 l THF and 100 ml Et3N are hydrogenated in the presence of 15 g Pd/C (10%; Engelhard 4505). The catalyst is filtered off and washed extensively with THF. Partial concentration of the filtrate precipitates the title compound: MS: [M+1]+=282.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed extensively with THF
  3. concentrationPartial concentration of the filtrate
  4. customprecipitates the title compound

Sources & evidence

ORD record
ord-68c715efa3d64ca591aa818f4019aad2
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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