Hydrochloric Acid → N-(6-chloro-5-(2,6-dimethoxy-benzyl)-4-pyrimidinyl)-p-vinylbenzenesulfonamide

HRID 326700Notes

Reaction equation

Cl[C:2]1[C:7]([CH2:8][C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[C:6]([Cl:19])[N:5]=[CH:4][N:3]=1.[K+].[CH:21]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH-:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[CH2:22].Cl>CO.CN(C)C=O>[Cl:19][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:32][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH:21]=[CH2:22])=[CH:24][CH:25]=2)(=[O:30])=[O:31])[C:7]=1[CH2:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 80 mg of 4,6-dichloro-5-(2,6-dimethoxybenzyl)pyrimidine and 170 mg of p-vinylbenzenesulfonamide monopotassium salt (J. Am. Chem. Soc. 1956, 78, 2169) from the corresponding sulfonamide with potassium t-butylate in absolute MeOH and 10 ml of dimethylformamide was heated at 100° C. for 6 hours. Thereafter, the mixture was left to cool to 25° C. overnight. Now, 30 ml of 0.5N HCl were added to the reaction solution while stirring. The precipitated substance was removed by filtration under suction and recrystallized from toluene/n-hexane. There were obtained 25 mg of N-(6-chloro-5-(2,6-dimethoxy-benzyl)-4-pyrimidinyl)-p-vinylbenzenesulfonamide, melting point 197°-198° C.

Workup

waitThereafter, the mixture was left
temperatureto cool to 25° C. overnight
customThe precipitated substance was removed by filtration under suction
customrecrystallized from toluene/n-hexane

Sources & evidence

ORD record: ord-6b8138c6b8894413a8c829408cebbabc
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270313

Reaction notes

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