Pyrimidin-5-amine → HCID 178512303, compound

HRID 1781576Notes

Reaction equation

HRID 1781576 reaction equation
C1C=CC(O[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][C:10]#[N:11])=CC=1.[NH2:19][C:20]1[CH:21]=[N:22][CH:23]=[N:24][CH:25]=1>CCOCC>[C:10]([N:9]=[C:8]([O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:19][C:20]1[CH:21]=[N:22][CH:23]=[N:24][CH:25]=1)#[N:11]

Participants

4

Reactant 2

HCID 344373Pyrimidin-5-amineHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 178512303HCID 178512303, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of diphenyl cyanocarbonimidate (1.05 g, 0.00442 mol), 5-amino-pyrimidine (0.42 g, 0.00442 mol) and Et2O (15 mL) was kept at ambient temperature for 4 days and at reflux for one day. There was little reaction. The solvent was evaporated and the residue was mixed with DME and warmed at 50°-55° for 2 days. The mixture was cooled, diluted with Et2O and filtered; the solid was washed with Et2O and dried to give 0.57 g of N'-Cyano-N-(5-pyrimidyl)-O-phenylisourea product.

Workup

  1. temperatureat reflux for one day
  2. customreaction
  3. customThe solvent was evaporated
  4. additionthe residue was mixed with DME
  5. temperaturewarmed at 50°-55° for 2 days
  6. temperatureThe mixture was cooled
  7. additiondiluted with Et2O
  8. filtrationfiltered
  9. washthe solid was washed with Et2O
  10. customdried

Sources & evidence

ORD record
ord-ba6618a5350d412685ae28c1c46959dc
Source dataset
uspto-grants-1997_05
Patent number
US05633374

Reaction notes

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