N-methyl-2-pyrrolidone → 2-Amino-3,5-difluoro-6-(p-methoxybenzylamino)-4-methylpyridine

HRID 368415Notes

Reaction equation

CN1CCCC1=O.[NH2:8][C:9]1[C:14]([F:15])=[C:13]([CH3:16])[C:12]([F:17])=[C:11](F)[N:10]=1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1>C(Cl)(Cl)Cl>[NH2:8][C:9]1[C:14]([F:15])=[C:13]([CH3:16])[C:12]([F:17])=[C:11]([NH:26][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[N:10]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To 3 ml of N-methylpyrrolidone were added 1.35 g of 2-amino-3,5,6-trifluoro-4-methylpyridine together with 3.0 g of p-methoxybenzylamine, and the mixture was stirred under nitrogen atmosphere at 140° C. for 18 hours and allowed to cool. After adding 30 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 chromatography (silica gel, 20 g; eluent: chloroform:n-hexane, 1:1, and then, chloroform) to obtain 0.90 g of the title compound as a pale yellow crude oil.

Workup

temperatureto cool
washthe 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-27aacc9ee6fd40bbb7e45e1520283585
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133284

Reaction notes

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