N-methyl-2-pyrrolidone → 2-{[2-(3-Bromo-4-hydroxyphenyl)ethyl]amino}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide

HRID 905688Notes

Reaction equation

CN1C(=O)CCC1.N1(O[C:18]2[N:23]=[C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=3)[C:21]([C:32]([NH2:34])=[O:33])=[CH:20][N:19]=2)C2C=CC=CC=2N=N1.[Br:35][C:36]1[CH:37]=[C:38]([CH2:43][CH2:44][NH2:45])[CH:39]=[CH:40][C:41]=1[OH:42].C(N(C(C)C)CC)(C)C>O>[Br:35][C:36]1[CH:37]=[C:38]([CH2:43][CH2:44][NH:45][C:18]2[N:23]=[C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=3)[C:21]([C:32]([NH2:34])=[O:33])=[CH:20][N:19]=2)[CH:39]=[CH:40][C:41]=1[OH:42]

Participants

Conditions

Temperature: 80 °C

Procedure

A 6 ml portion of NMP solution containing 600 mg of 2-(benzotriazol-1-yloxy)-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide was mixed with 538 mg of 2-(3-bromo-4-hydroxyphenyl)ethylamine and 0.72 ml of diisopropylethylamine, followed by stirring at 80° C. for 2 hours. The reaction mixture was cooled down to room temperature, and then mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, the solvent was evaporated, and then the resulting residue was recrystallized (ethanol-THF) to obtain 200 mg of 2-{[2-(3-bromo-4-hydroxyphenyl)ethyl]amino}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide as colorless crystals.

Workup

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 recrystallized (ethanol-THF)

Sources & evidence

ORD record: ord-8b89503d5914481aa48ddc66e383a658
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012959B2

Reaction notes

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