N-methyl-2-pyrrolidone → HCID 67388920, compound

HRID 269843Notes

Reaction equation

HRID 269843 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1.[NH2:19][C:20]1(OCC)[CH:25]=[CH:24][C:23](O)=[CH:22][CH2:21]1.C(N(C(C)C)CC)(C)C.CN1[C:44](=[O:45])[CH2:43]CC1>C(OCC)(=O)C.O>[OH:45][CH2:44][CH2:43][C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=3)[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=2)=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 184608435-Pyrimidinecarboxamide, 2-chloro-4-[(3-methylphenyl)amino]-HCID 66789000HCID 66789000, compound

Product 1

HCID 67388920HCID 67388920, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2.0 g of 2-chloro-4-{(3-methylphenyl)amino}pyrimidine-5-carboxamide, 1.25 g of 4-aminophenetyl alcohol, 1.99 ml of diisopropylethylamine and 10 ml of NMP was stirred overnight at 110° C. The reaction mixture was cooled down to room temperature and mixed with water and ethyl acetate, and the thus precipitated solid was collected by filtration and recrystallized (methanol) to obtain 560 mg of 2-{[4-(2-hydroxyethyl)phenyl]amino}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide as pale yellow crystals.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationthe thus precipitated solid was collected by filtration
  3. customrecrystallized (methanol)

Sources & evidence

ORD record
ord-eabba9ed2ea94237bf43edbb356afb04
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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