Ammonia → 2,4-Diamino-6-chloro-5-(2,4-dichlorophenyl)-pyrimidine

HRID 846366Notes

Reaction equation

HRID 846366 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[C:4]([Cl:17])[N:3]=1.[NH3:18]>[Cu].CCO>[NH2:1][C:2]1[N:7]=[C:6]([NH2:18])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[C:4]([Cl:17])[N:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 197050544,6-Dichloro-5-(2,4-dichlorophenyl)pyrimidin-2-amine

Product 1

HCID 197051262,4-Diamino-6-chloro-5-(2,4-dichlorophenyl)-pyrimidineYield 25%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-amino-5-(2,4-dichlorophenyl)-4,6-dichloropyrimidine (0.5 g) (Example 32) EtOH saturated with ammonia (20 ml) and copper powder (0.05 g) was heated in an autoclave at 180° C. for 18 hours. The cooled reaction mixture was filtered, evaporated and the residue purified by flash column chromatography to give the title compound (0.12, 25%) mp. 219° C.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. customevaporated
  4. customthe residue purified by flash column chromatography

Sources & evidence

ORD record
ord-74470ffd035540129f4fc21f066d9ce3
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

Loading…