P-Anisidine → HCID 67388964, compound

HRID 269844Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=[C:11](S(C)(=O)=O)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1.[F-].[K+].C(=O)(O)[O-].[Na+]>O.CN1C(=O)CCC1>[CH2:1]([NH:8][C:9]1[C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=[C:11]([NH:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A 5 ml portion of NMP solution containing 300 mg of 4-benzylamino-2-(methylsulfonyl)pyrimidine-5-carboxamide was mixed with 122 mg of p-anisidine and 58 mg of potassium fluoride, followed by stirring at 90 to 100° C. for 21 hours. During this period, 58 mg of potassium fluoride was added three times. The reaction mixture was cooled down to room temperature, diluted with water, mixed with saturated sodium bicarbonate aqueous solution and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (chloroform:methanol) and then recrystallized (methanol-THF) to obtain 82 mg of 4-benzylamino-2-[(4-methoxyphenyl)amino]pyrimidine-5-carboxamide as colorless crystals.

Workup

waitDuring this period
temperatureThe reaction mixture was cooled down to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
customthe solvent was evaporated
customThe resulting residue was purified by a silica gel column chromatography (chloroform:methanol)
customrecrystallized (methanol-THF)

Sources & evidence

ORD record: ord-5e6f16be713442e3825606d281106d69
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449456B2

Reaction notes

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