Pyridine → 6-(2-Amino-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester

HRID 556364Notes

Reaction equation

HRID 556364 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C:15]3[CH:20]=[C:19](Cl)[N:18]=[C:17]([NH2:22])[N:16]=3)=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4].N1C=CC=CC=1>C1COCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:22])[N:16]=3)=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 1049PyridineHCID 866266276-(2-Amino-6-chloro-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester

Product 1

HCID 575564496-(2-Amino-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9.2 g (28.8 mMol) 6-(2-amino-6-chloro-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester and 23.4 ml (0.29 Mol) pyridine in 1 l THF is hydrogenated in presence of 3.9 g Pd/C 10% during 5 h. The mixture is filtered through a pad of celite and char coal, the solid washed extensively with THF and MeOH and the filtrate concentrated. The residue is stirred with 400 ml EtOAc and 200 ml water. Filtration of the suspension and washing with water and EtOAc yields the title compound: m.p.: 194-196° C.; MS: [M+1]+=286. The aq. layer is separated off from the filtrate and extracted 3 times with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated. Trituration from ether and EtOAc yields more of the title compound.

Workup

  1. filtrationThe mixture is filtered through a pad of celite and char coal
  2. washthe solid washed extensively with THF and MeOH
  3. concentrationthe filtrate concentrated
  4. filtrationFiltration of the suspension
  5. washwashing with water and EtOAc

Sources & evidence

ORD record
ord-e6054c7838d94fbc92b669a04a04e52e
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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