Triethylamine → N-(2,6-bis-methylamino-pyrimidin-4-yl)-3-trifluoromethyl-benzenesulfonamide

HRID 610825Notes

Reaction equation

HRID 610825 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.Cl.CN.[CH2:27]([N:29](CC)CC)C>CCO>[CH3:9][NH:8][C:6]1[N:5]=[C:4]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)(=[O:13])=[O:12])[CH:3]=[C:2]([NH:29][CH3:27])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 19353537N-(6-chloro-2-methylamino-pyrimidin-4-yl)-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 17774506N-(2,6-bis-methylamino-pyrimidin-4-yl)-3-trifluoromethyl-benzenesulfonamideYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

0.10 g (0.00027 mol) of N-(6-chloro-2-methylamino-pyrimidin-4-yl)-3-trifluoromethyl-benzenesulfonamide was dissolved in 5 ml of EtOH, treated with 0.27 g (0.004 mol) of methylamine hydrochloride and 1 ml (0.007 mol) of triethylamine and stirred in an autoclave at 145° C. for 17 hours. The entire reaction mixture was partitioned in ethyl acetate/water and extracted. The residue was recrystallized in MeOH. There was obtained 0.055 g (56%) of N-(2,6-bis-methylamino-pyrimidin-4-yl)-3-trifluoromethyl-benzenesulfonamide as white crystals; m.p. 234-235° C.

Workup

  1. customThe entire reaction mixture
  2. customwas partitioned in ethyl acetate/water
  3. extractionextracted
  4. customThe residue was recrystallized in MeOH

Sources & evidence

ORD record
ord-e795ad92990f49ada22fa361d64e22cf
Source dataset
uspto-grants-1999_12
Patent number
US05998665

Reaction notes

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