2,4-Dimethoxybenzylamine → N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine

HRID 537027

Reaction equation

F[C:2]1[CH:7]=[C:6]([I:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[CH2:20][NH2:21]>CCOC(C)=O>[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[CH2:20][NH:21][C:2]1[CH:7]=[C:6]([I:8])[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-fluoro-4-iodo-5-methylpyridine (60 g, 253 mmol) and 1-(2,4-dimethoxyphenyl)methanamine (190.6 mL, 1270 mmol) was allowed to stir at 110° C. overnight. The mixture was allowed to cool to rt and was then diluted with EtOAc (190 mL). The resulting solid was filtered and washed with EtOAc and then purified by column chromatography to give N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine (55.0 g, 57%).

Workup

temperatureto cool to rt
filtrationThe resulting solid was filtered
washwashed with EtOAc
custompurified by column chromatography

Sources & evidence

ORD record: ord-325d4bda78d84a6fa902d9be0996752d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859768B2

Linked notes

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