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

HRID 269835노트

반응식

HRID 269835 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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 aceatate. 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.

후처리

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

출처 및 근거

ORD 기록
ord-b64140813afb4c169ca7e5c37d9f07f3
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449456B2

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