Guanidine Hydrochloride → 6-(2-Furyl)-5-(4-pyridyl)-2,4-pyrimidinediamine

HRID 457874Notes

Reaction equation

HRID 457874 reaction equation
[Na].Cl.[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=O.Cl.[NH2:20][C:21]([NH2:23])=[NH:22]>C(O)C>[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[N:20]=[C:21]([NH2:23])[N:22]=[C:10]([NH2:11])[C:9]=1[C:6]1[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 7362FurfuralHCID 5360545SodiumHCID 123966084-Pyridylacetonitrile hydrochloride

Product 1

HCID 99212956-(2-Furyl)-5-(4-pyridyl)-2,4-pyrimidinediamineYield 21.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After sodium (3.2 g, 139 mmol) was dissolved in anhydrous ethanol (200 mL), 4-pyridyl acetonitrile hydrochloride (10.0 g, 64 mmol) and 2-furaldehyde (6.1 mL, 73.6 mmol) and guanidine hydrochloride (7.0 g, 73.3 mmol) were successively added thereto. After stirring at room temperature for 1 hour, it was heated under reflux for 7 hours. After cooling as it was, the insoluble matters were filtered off, washed with tetrahydrofuran, and the solvent was removed from the filtrate. Tetrahydrofuran (200 mL) and activated manganese dioxide (30.0 g) were added to the residue, followed by heating under reflux for 2.5 hours. After cooling as it was, the manganese dioxide was filtered through Celite, and washed with tetrahydrofuran. The collected filtrate was concentrated, and then methanol was added to the residues. The resulting precipitates were collected by filtration and washed with methanol, to give the title compound (3.48 g, 21%) as a pale brown solid.

Workup

  1. temperatureit was heated
  2. temperatureunder reflux for 7 hours
  3. temperatureAfter cooling as it
  4. filtrationthe insoluble matters were filtered off
  5. washwashed with tetrahydrofuran
  6. customthe solvent was removed from the filtrate
  7. additionTetrahydrofuran (200 mL) and activated manganese dioxide (30.0 g) were added to the residue
  8. temperatureby heating
  9. temperatureunder reflux for 2.5 hours
  10. temperatureAfter cooling as it
  11. filtrationthe manganese dioxide was filtered through Celite
  12. washwashed with tetrahydrofuran
  13. concentrationThe collected filtrate was concentrated
  14. additionmethanol was added to the residues
  15. customThe resulting precipitates
  16. filtrationwere collected by filtration
  17. washwashed with methanol

Sources & evidence

ORD record
ord-d3c8691e14c940689b9658a9076c4171
Source dataset
uspto-grants-2007_03
Patent number
US07189717B2

Reaction notes

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