Bromine → HCID 178461590、化合物

HRID 522810ノート

反応式

HRID 522810 の反応式
[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

参加物

5

反応物 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 178461592HCID 178461592、化合物

生成物 1

HCID 178461590HCID 178461590、化合物収率 39.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9d7b07c8173d4d5faf5ab734bd8057fa
出典データセット
uspto-grants-2016_05
特許番号
US09334271B2

反応ノート

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