Triethylamine → N-(2,6-bis-methylamino-pyrimidin-4-yl)-4-tert-butyl-benzenesulfonamide

HRID 1584200Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20](N)=[C:19](Cl)[N:18]=[C:17](C)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:25][NH2:26].C([N:29]([CH2:32]C)CC)C>C(O)C>[CH3:25][NH:26][C:17]1[N:16]=[C:15]([NH:14][S:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][CH:7]=2)(=[O:13])=[O:12])[CH:20]=[C:19]([NH:29][CH3:32])[N:18]=1

Participants

Conditions

Temperature: 140 °C

Procedure

0.47 g (0.001 3 mol) of 4-tert-butyl-N-(6-chloro-2-methyl-amino-pyrimidin-4-yl)-benzenesulfonamide was dissolved in 10 ml of ethanol, treated with 1.3 g (0.019 mol) of methylamine hydrochloride and 4.7 ml (0.034 mol) of triethylamine and stirred in an autoclave at 140° C. for 18 hours. The mixture was freed completely from solvent, the residue was partitioned in ethyl acetate/water and the insoluble constituents were filtered off under suction. The filtered cake was recrystallized in methanol/diethyl ether. There was obtained 0.15 g (33%) of N-(2,6-bis-methylamino-pyrimidin-4-yl)-4-tert-butyl-benzenesulfonamide as white crystals; m.p. 316-318° C.

Workup

customthe residue was partitioned in ethyl acetate/water
filtrationthe insoluble constituents were filtered off under suction
customThe filtered cake was recrystallized in methanol/diethyl ether

Sources & evidence

ORD record: ord-214eed43d33e4c6d9bad17d20519c1df
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932599

Reaction notes

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