Sodium Hydroxide → N,4-bis(2-chloropyridin-4-yl)pyrimidin-2-amine

HRID 2389564Notes

Reaction equation

HRID 2389564 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH:9]=[CH:10]N(C)C)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[Cl:31][C:32]1[CH:37]=[C:36]([NH:38][C:39]([NH2:41])=[NH:40])[CH:35]=[CH:34][N:33]=1>CC(O)C>[Cl:31][C:32]1[CH:37]=[C:36]([NH:38][C:39]2[N:41]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=3)[CH:9]=[CH:10][N:40]=2)[CH:35]=[CH:34][N:33]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 544350393-Dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-oneHCID 178512588HCID 178512588, compound

Product 1

HCID 86644113N,4-bis(2-chloropyridin-4-yl)pyrimidin-2-amineYield 49.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 6.32 g of 1-(2-chloropyridin-4-yl)-3-(dimethylamino)prop-2-en-1-one (30 mmol) in 60 ml of 2-Propanol was added 2.52 g of sodium hydroxide (63 mmol) and 11.96 g of 1-(2-chloropyridin-4-yl)guanidine bis(trifluoroacetate) (30 mmol). The reaction mixture was heated to reflux under stirring for 20 h. After filtration, the precipitate was washed with 100 ml of n-butanol and 120 ml of iPr2O and then air-dried to yield 4.69 g of N,4-bis(2-chloropyridin-4-yl)pyrimidin-2-amine (yield=37%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. filtrationAfter filtration
  4. washthe precipitate was washed with 100 ml of n-butanol and 120 ml of iPr2O
  5. customair-dried

Sources & evidence

ORD record
ord-083cf6e597e041eca9798282e4ae072e
Source dataset
uspto-grants-2012_09
Patent number
US08273759B2

Reaction notes

Loading…