Benzene → 2-Amino-4-bromo-5-chloro-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine

HRID 1274780Notes

Reaction equation

CN1CCCC1=O.[NH2:8][C:9]1[C:14]([F:15])=[C:13]([Br:16])[C:12]([Cl:17])=[C:11](F)[N:10]=1.[CH3:19][C:20]([NH2:27])([CH3:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23].C1C=CC=CC=1>CCCCCC>[NH2:8][C:9]1[C:14]([F:15])=[C:13]([Br:16])[C:12]([Cl:17])=[C:11]([NH:27][C:20]([CH3:26])([CH3:19])[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[N:10]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To 6 ml of N-methylpyrrolidone were added 2.4 g of 2-amino-4-bromo-5-chloro-3,6-difluoropyridine and 3.5 g of 1,1,3,3-tetramethylbutylamine, and the mixture was stirred at 140° C. for 82 hours and allowed to cool. 50 ml of the mixed solution of benzene and n-hexane (1:1, v/v) was added, and the solution was washed twice with 400 ml of distilled water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The brown oily residue was subjected to column chromatography (silica gel, 30 g; eluent: chloroform:n-hexane, 1:1) to obtain 1.6 g of the title compound as a colorless oily residue.

Workup

temperatureto cool
washthe solution was washed twice with 400 ml of distilled water
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0856dc758a6d427aa2c0151ae0556b21
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156903

Reaction notes

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