P-Anisidine → HCID 67388964, compound

HRID 905697Notes

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-ee68f5f9bbb84651b13a5f58f5418765
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012959B2

Reaction notes

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