Bromine → HCID 178461590, 화합물

HRID 522810노트

반응식

HRID 522810 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@H:12]2[CH3:17])[N:3]=1.[Br:18]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:18][C:7]1[NH:8][C:9]2[C:5]([N:6]=1)=[C:4]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@H:12]1[CH3:17])[N:3]=[C:2]([Cl:1])[N:10]=2

참가 물질

5

반응물 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 178461592HCID 178461592, 화합물

생성물 1

HCID 178461590HCID 178461590, 화합물수율 39.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-chloro-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (950 mg, 3.74 mmol) in CH2Cl2(19 mL) was added bromine (0.23 mL, 4.49 mmol). The mixture was stirred at ambient temperature for 19 hours. Saturated sodium thiosulfate was added. The aqueous layer was extracted with dichloromethane two times. Organic layers were combined and dried over Na2SO4 and solvent was removed under reduced pressure. The crude was purified by flash column chromatography (0-70% EtOAc/cyclohexane gradient) to furnish product as a white solid (495 mg, 39%). LC-MS at 254 nm; [M+H] 334.1; Rt 0.89 min; (LCMS method 1).

후처리

  1. extractionThe aqueous layer was extracted with dichloromethane two times
  2. dry with materialdried over Na2SO4 and solvent
  3. customwas removed under reduced pressure
  4. customThe crude was purified by flash column chromatography (0-70% EtOAc/cyclohexane gradient)

출처 및 근거

ORD 기록
ord-9d7b07c8173d4d5faf5ab734bd8057fa
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334271B2

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