p-Toluenesulfonic acid → HCID 86688211, compound

HRID 1630346Notes

Reaction equation

HRID 1630346 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=1.[Cl:14][C:15]1[N:20]=[CH:19][C:18]([NH2:21])=[C:17]([O:22][CH3:23])[CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Cl:14][C:15]1[N:20]=[CH:19][C:18]([NH:21][C:2]2[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=2)=[C:17]([O:22][CH3:23])[CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 210775872-Chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amineHCID 826521296-chloro-4-Methoxypyridin-3-aMine

Product 1

HCID 86688211HCID 86688211, compoundYield 137.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (211 mg, 1 mmol), 6-chloro-4-methoxypyridin-3-amine (150 mg, 0.95 mmol) and para-toluenesulphonic acid (190 mg, 1 mmol) in 1,4-dioxane (2 mL) was heated at 100° C. for 1 h. The mixture was cooled and filtered, the solid was washed with dioxane and dried in vacuo to give the product as a cream coloured solid (436 mg, >100%). 1H NMR (400 MHz, DMSO): δ 9.82 (s, 1H); 8.76 (s, 1H); 8.44 (s, 2H); 7.38 (s, 1H); 4.00 (s, 3H); 2.99-2.92 (m, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washthe solid was washed with dioxane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4cf3de9b3ab3456ca8387c007900072e
Source dataset
uspto-grants-2014_07
Patent number
US08791130B2

Reaction notes

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