(+-)-2-Butanol → N-(2-(2-bromophenoxy)pyrimidin-5-yl)-4-phenylphthalazin-1-amine

HRID 911181

반응식

HRID 911181 반응식
[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][C:5]1[N:10]=[CH:9][C:8]([NH2:11])=[CH:7][N:6]=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:19][N:18]=1.CC(O)CC.C1C2C(=CC=CC=2)C=NN=1>CCCCCC>[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]([NH:11][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:19][N:18]=2)=[CH:9][N:10]=1

참가 물질

6

반응물 4

HCID 6568(+-)-2-ButanolHCID 9207PhthalazineHCID 2721091-Chloro-4-phenylphthalazineHCID 611477222-(2-Bromophenoxy)pyrimidin-5-amine

생성물 1

HCID 57756263N-(2-(2-bromophenoxy)pyrimidin-5-yl)-4-phenylphthalazin-1-amine

시약·촉매·용매 1

HCID 8058Hexane용매

반응 조건

온도
120 °C

실험 절차

2-(2-Bromophenoxy)pyrimidin-5-amine (3.01 g, 11.3 mmol), 1-chloro-4-phenylphthalazine (2.72 g, 11.3 mmol), and butan-2-ol (56.6 ml, 11.3 mmol) were placed in a sealed tube. The reaction vessel was sealed and mixture heated to 120° C. After 1.5 h, LCMS showed mainly product as [M+H]+=470 and a small amount of bromo starting material. 200 mg of phthalazine was added. After another 3.5 h, the reaction was cooled to RT. Hexane was added to allow a yellow solids to precipitate. The yellow solids were filtered and recrystallized with DCM and hexanes. The resulting dark brown solids were dried under vacuum overnight, affording the product, N-(2-(2-bromophenoxy)pyrimidin-5-yl)-4-phenylphthalazin-1-amine.

후처리

  1. customThe reaction vessel was sealed
  2. waitAfter another 3.5 h
  3. temperaturethe reaction was cooled to RT
  4. customto precipitate
  5. filtrationThe yellow solids were filtered
  6. customrecrystallized with DCM and hexanes
  7. customThe resulting dark brown solids were dried under vacuum overnight

출처 및 근거

ORD 기록
ord-cc129f5604084194a0eaf3a57e710e4c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022221B2

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