N-methyl-2-pyrrolidone → HCID 67389249, compound

HRID 269836Notes

Reaction equation

CN1C(=O)CCC1.Cl[C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[CH:17]=2)[C:12]([C:24]([NH2:26])=[O:25])=[CH:11][N:10]=1.Cl.[Cl:28][C:29]1[CH:30]=[C:31]([CH2:36][CH2:37][NH2:38])[CH:32]=[CH:33][C:34]=1[OH:35].C(N(C(C)C)CC)(C)C>O>[Cl:28][C:29]1[CH:30]=[C:31]([CH2:36][CH2:37][NH:38][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[CH:17]=3)[C:12]([C:24]([NH2:26])=[O:25])=[CH:11][N:10]=2)[CH:32]=[CH:33][C:34]=1[OH:35]

Participants

Conditions

Temperature: 80 °C

Procedure

A 6 ml portion of NMP solution containing 533 mg of 2-chloro-4-[(3-ethylphenyl)amino]pyrimidine-5-carboxamide was mixed with 0.624 mg of 2-(3-chloro-4-hydroxyphenyl)ethylamine hydrochloride and 0.87 ml of diisopropylethylamine, followed by stirring at 80° C. for 4 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 (methanol-THF) to obtain 460 mg of 2-{[2-(3-chloro-4-hydroxyphenyl)ethyl]amino}-4-[(3-ethylphenyl)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 (methanol-THF)

Sources & evidence

ORD record: ord-d3ae57d97f8440fbacdf3e288aa9d6ec
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449456B2

Reaction notes

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