p-Toluidine → 6-Chloro-n4-(4-methylphenyl)pyrimidine-2,4-diamine

HRID 2375482

Reaction equation

HRID 2375482 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.[OH-].[Na+]>O1CCOCC1>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 2387486-Chloro-n4-(4-methylphenyl)pyrimidine-2,4-diamineYield 85.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4,6-dichloro-2-pyrimidinamine (1.64 g, 0.01 mol), p-toluidine (1.07 g, 0.01 mol) in dioxane (2 mL) was heated in a sealed tube for 30 minutes at 140° C. The crude product was treated with NaOH (50 ml, 2M) and extracted with CH2Cl2 (3×50 mL). The organic layer was washed with brine (2×100 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica using hexane/EtOAc (1:3), giving the desired product (2 g, 78%).

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. washThe organic layer was washed with brine (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography on silica

Sources & evidence

ORD record
ord-5c1dee1e6e954695b9d24eb6a59d79da
Source dataset
uspto-grants-2008_12
Patent number
US07465750B2

Linked notes

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