Benzylamine → 2-Benzylamino-6-(t-butylamino)-3-chloro-5-fluoropyridine

HRID 610222Notes

Reaction equation

[C:1]([NH:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([Cl:13])=[C:8](F)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN1CCCC1=O>[CH2:15]([NH:22][C:8]1[C:9]([Cl:13])=[CH:10][C:11]([F:12])=[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[N:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To 10 ml of N-methylpyrrolidone was added 6.8 g of 2-(t-butylamino)-5-chloro-3,6-difluoropyridine together with 8.0 g of benzylamine, and the mixture was stirred at 150° C. for one day, and allowed to cool. After 80 ml of chloroform, the mixture was washed three times with 300 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (silica gel, 100 g; eluent: chloroform:n-hexane, 1:1) to obtain about 7.0 g of the title compound as a pale brown crude oil.

Workup

temperatureto cool
washAfter 80 ml of chloroform, the mixture was washed three times with 300 ml of distilled water
dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-84977903f248406896fe573dcc873279
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998436

Reaction notes

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