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

HRID 905696Notes

Reaction equation

HRID 905696 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[CH:28]=[CH:27][C:23]([CH2:24][CH2:25][OH:26])=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.CN1C(=O)CCC1>C(OCC)(=O)C.O>[OH:26][CH2:25][CH2:24][C:23]1[CH:27]=[CH:28][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:21][CH:22]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 669044-Aminophenethyl alcoholHCID 81531DiisopropylethylamineHCID 184608435-Pyrimidinecarboxamide, 2-chloro-4-[(3-methylphenyl)amino]-

Product 1

HCID 67388920HCID 67388920, compoundYield 20.2%

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-aminophenethyl 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-53acdbe076e94a9a89c3d4ed4eae4b05
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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