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

HRID 905688ノート

反応式

HRID 905688 の反応式
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]

参加物

6

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 53238424-(2-Aminoethyl)-2-bromophenolHCID 574721002-(Benzotriazol-1-yloxy)-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide

生成物 1

HCID 444226642-{[2-(3-Bromo-4-hydroxyphenyl)ethyl]amino}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide収率 27.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customthe resulting residue was recrystallized (ethanol-THF)

出典と根拠

ORDレコード
ord-8b89503d5914481aa48ddc66e383a658
出典データセット
uspto-grants-2011_09
特許番号
US08012959B2

反応ノート

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