2,6-Dimethylaniline → 2,4-Dichloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide

HRID 2357978Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](Cl)=[O:10])=[CH:4][N:3]=1.[CH3:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:14]=1[NH2:15]>CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([NH:15][C:14]2[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:13]=2[CH3:12])=[O:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 20.3 g (96 mmol) of 2,4-dichloropyrimidine-5-carbonyl chloride 29 and Amberlyst A21 (2.1 g) in 400 mL of EtOAc was added dropwise 11.7 mL of 2,6-dimethylaniline (95 mmol) at room temperature. The resulting mixture was heated to 50° C. for 12 h, and then was filtered. The filtrate was washed sequentially with water (200 mL), 1N HCl (50 mL), 1N NaOH (50 mL), and brine (100 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was washed with a small amount of DCM to give the title compound as a white solid. Mass Spectrum (ESI) m/e=297.1 (M+1).

Workup

filtrationwas filtered
washThe filtrate was washed sequentially with water (200 mL), 1N HCl (50 mL), 1N NaOH (50 mL), and brine (100 mL)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
washthe filtrate was washed with a small amount of DCM

Sources & evidence

ORD record: ord-8ce5212c9a1f40c291fdba85cb28e505
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763624B2

Reaction notes

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