Guanidine Hydrochloride → 4,6-Di(2-furyl)-5-(4-pyridyl)-2-pyrimidinylamine

HRID 747158Notes

Reaction equation

HRID 747158 reaction equation
[Na].[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=O)[CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1.[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=O.Cl.[NH2:24][C:25]([NH2:27])=[NH:26]>C(O)C>[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:21]([C:17]2[O:16][CH:20]=[CH:19][CH:18]=2)[N:26]=[C:25]([NH2:27])[N:24]=1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 7362FurfuralHCID 5360545SodiumHCID 227080301-(2-Furyl)-2-pyridin-4-ylethanone

Product 1

HCID 230204264,6-Di(2-furyl)-5-(4-pyridyl)-2-pyrimidinylamineYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After dissolving sodium (540 mg, 23.5 mmol) in anhydrous ethanol (200 ml), 1-(2-furyl)-2-(4-pyridyl)-1-ethanone (2.00 g, 10.7 mmol) and 2-furaldehyde (0.97 ml, 11.7 mmol) were successively added thereto and the mixture was stirred at room temperature. After 1.5 hours, guanidine hydrochloride (7.0 g, 73.3 mmol) was added thereto, followed by heating under reflux for 14 hours. After cooling as it was, the reaction mixture was concentrated and the residue was suspended in tetrahydrofuran. Then, the insoluble matters were filtered off and washed with tetrahydrofuran, and the solvent of the filtrate was evaporated. To the residue were added tetrahydrofuran (80 ml) and active manganese dioxide (30.0 g), followed by heating under reflux for 2 hours. After cooling as it was, the manganese dioxide was filtered off through Celite and washed with tetrahydrofuran. The combined filtrates were concentrated, and then methanol was added to the residue. The resulting precipitates were collected by filtration and washed with methanol, to give the title compound (1.32 g, 41%) as a pale brown solid.

Workup

  1. additionwere successively added
  2. temperatureby heating
  3. temperatureunder reflux for 14 hours
  4. temperatureAfter cooling as it
  5. concentrationthe reaction mixture was concentrated
  6. filtrationThen, the insoluble matters were filtered off
  7. washwashed with tetrahydrofuran
  8. customthe solvent of the filtrate was evaporated
  9. additionTo the residue were added tetrahydrofuran (80 ml) and active manganese dioxide (30.0 g)
  10. temperatureby heating
  11. temperatureunder reflux for 2 hours
  12. temperatureAfter cooling as it
  13. filtrationthe manganese dioxide was filtered off through Celite
  14. washwashed with tetrahydrofuran
  15. concentrationThe combined filtrates were concentrated
  16. additionmethanol was added to the residue
  17. customThe resulting precipitates
  18. filtrationwere collected by filtration
  19. washwashed with methanol

Sources & evidence

ORD record
ord-2fa943efb61845889c323864f9094a0b
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

Loading…