Boron tribromide → 3-{[(2-{[3-(3-Bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol

HRID 1614939노트

반응식

HRID 1614939 반응식
[Cl:1][C:2]1[C:3]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27]C)[CH:22]=2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17]O)[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.B(Br)(Br)[Br:30].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:30][CH2:17][CH2:16][CH2:15][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:19][CH2:20][C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)[CH:14]=[CH:13][CH:12]=1

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 584679043-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]propan-1-ol

생성물 1

HCID 584678443-{[(2-{[3-(3-Bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol수율 74%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

Into a 1-neck round-bottom flask were added 3-[3-({5-chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]propan-1-ol (0.18 g, 0.45 mmol) and DCM (5 mL). To the reaction mixture was added a solution of boron tribromide in methylene chloride (3.0 mL, 3.0 mmol, 1.0 M) at 0° C. The mixture was allowed to warm up to rt and stirred overnight. The resultant mixture was cooled in a dry ice bath when NaHCO3 (saturated aqueous solution, 10 mL) was added. The mixture was allowed to warm up to rt and DCM was added. The aqueous layer was extracted with DCM twice. The organic layers were combined, dried, filtered, and concentrated under vacuum to give the desired product as an off-white powder (150 mg, 74%). LCMS for C20H21BrClN4O (M+H)+: m/z=447.0, 449.0.

후처리

  1. additionwas added
  2. temperatureto warm up to rt
  3. extractionThe aqueous layer was extracted with DCM twice
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-952d50559a354710a40d35e34981f659
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765727B2

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