4-Methoxybenzyl alcohol → HCID 59749106, compound

HRID 747160Notes

Reaction equation

HRID 747160 reaction equation
[Na].Cl[C:3]1[N:8]=[CH:7][C:6]([C:9]2[C:10]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)=[N:11][C:12]([NH2:15])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.C[O:22]C1C=CC(CO)=CC=1>[Cl-].[NH4+].C(OCC)(=O)C>[NH2:15][C:12]1[N:11]=[C:10]([C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[C:9]([C:6]2[CH:5]=[CH:4][C:3](=[O:22])[NH:8][CH:7]=2)=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 5360545SodiumHCID 23020407HCID 23020407, compound

Product 1

HCID 59749106HCID 59749106, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

After sodium (455 mg, 19.8 mmol) was dissolved in 4-methoxybenzyl alcohol (15 ml) at 90° C. under an atmosphere of nitrogen gas, 5-(6-chloro-3-pyridyl)-4-(2-furyl)-2-pyrimidinylamine (1.80 g, 6.60 mmol) was added thereto and the mixture was stirred as it was. After 1.5 hours, the reaction mixture was cooled as it was and then diluted with an aqueous saturated ammonium chloride solution and ethyl acetate. The resulting organic layer was washed with an aqueous saturated ammonium chloride solution, dried over anhydrous sodium sulfate and concentrated. Trifluoroacetic acid (40 ml) was added to the residue, followed by stirring at 65° C. After 18 hours, the reaction mixture was cooled as it was and diluted with dichloromethane, water and 5N hydrochloride. The resulting aqueous layer was washed with ethyl acetate and adjusted to pH 6 with 5N sodium hydroxide. The resulting crystals were collected by filtration and washed with water, to give crude crystals of the title compound. The resulting crude crystals were suspended in ethyl acetate, collected by filtration and washed with ethyl acetate, to give the title compound (820 mg, 49%) as a colorless solid.

Workup

  1. temperaturethe reaction mixture was cooled as it
  2. washThe resulting organic layer was washed with an aqueous saturated ammonium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionTrifluoroacetic acid (40 ml) was added to the residue
  6. stirringby stirring at 65° C
  7. waitAfter 18 hours
  8. temperaturethe reaction mixture was cooled as it
  9. additiondiluted with dichloromethane, water and 5N hydrochloride
  10. washThe resulting aqueous layer was washed with ethyl acetate
  11. filtrationThe resulting crystals were collected by filtration
  12. washwashed with water

Sources & evidence

ORD record
ord-c3bfd866827f4fd7bc05cad77df3d55a
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

Loading…