Isobutylamine → 6-Chloro-N~4~-(2-methylpropyl)pyrimidine-2,4(1H,3H)-diimine

HRID 128928Notes

Reaction equation

HRID 128928 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH2:10]([NH2:14])[CH:11]([CH3:13])[CH3:12]>C(O)C>[NH2:1][C:2]1[N:3]=[C:4]([NH:14][CH2:10][CH:11]([CH3:13])[CH3:12])[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 2358976-Chloro-N~4~-(2-methylpropyl)pyrimidine-2,4(1H,3H)-diimineYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50 g of 2-amino-4,6-dichloropyrimidine are suspended in 250 ml of ethanol. 45.65 g of isobutylamine are added. The reaction mixture is heated under reflux for 3 hours. It is evaporated to dryness. The oily residue is taken up in 250 ml of water. The mixture is stirred vigorously for 1 hour. The precipitate formed is filtered on sintered glass, washed with 100 ml of water and then dried under vacuum over phosphorus pentoxide. It is recrystallized from 500 ml of isopropyl ether. 50.15 g of 2-amino-4-isobutylamino-6-chloropyrimidine are obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 3 hours
  3. customIt is evaporated to dryness
  4. customThe precipitate formed
  5. filtrationis filtered on sintered glass
  6. washwashed with 100 ml of water
  7. dry with materialdried under vacuum over phosphorus pentoxide
  8. customIt is recrystallized from 500 ml of isopropyl ether

Sources & evidence

ORD record
ord-a141d919dbf24a44bacfdcf10559ce62
Source dataset
uspto-grants-1995_11
Patent number
US05466694

Reaction notes

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