HCID 47453787, compound → HCID 59596398, compound

HRID 2264606Notes

Reaction equation

HRID 2264606 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[N:5]=[C:4]([NH2:19])[N:3]=1>C1COCC1.[Pd]>[NH:15]1[C:16]2[C:11](=[CH:10][C:9]([O:8][C:6]3[CH:7]=[CH:2][N:3]=[C:4]([NH2:19])[N:5]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]1

Participants

4

Reactant 1

HCID 47453787HCID 47453787, compound

Product 1

HCID 59596398HCID 59596398, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.4 g (0.02 mol) 4-chloro-6-(quinolin-6-yloxy)-pyrimidin-2-ylamine in 600 mL of THF is hydrogenated during 21 h in the presence of 1.2 g Pd/C (10% Engelhard 4505). Then the catalyst is filtered off and the filtrate concentrated in vacuuo. The residue is partitioned between ethyl acetate and conc. sodium bicarbonate solution and the organic layer washed with brine, dried and evaporated. The crude product is purified by flash-chromatography on silica gel using dichloromethane/methanol 95:5 as eluent. Fractions with pure compound are pooled and evaporated. The crystalline material is triturated with ether, filtered and dried to give the title compound: m.p. 180-182° C.; MS: [M+1]+=243; TLC (dichloromethane/methanol 95:5): Rf=0.4.

Workup

  1. filtrationThen the catalyst is filtered off
  2. concentrationthe filtrate concentrated in vacuuo
  3. customThe residue is partitioned between ethyl acetate and conc. sodium bicarbonate solution
  4. washthe organic layer washed with brine
  5. customdried
  6. customevaporated
  7. customThe crude product is purified by flash-chromatography on silica gel
  8. customevaporated
  9. customThe crystalline material is triturated with ether
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-256ba812e35746868ea1714b7eca2bcd
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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