Bromine → HCID 178461551、化合物

HRID 876516ノート

反応式

HRID 876516 の反応式
[CH3:1][C@@H:2]1[O:7][C@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][NH:15]3)=[C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:10]=2)[CH2:3]1.[Br:24]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:24][C:14]1[NH:15][C:16]2[C:12]([N:13]=1)=[C:11]([N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)[N:10]=[C:9]([N:4]1[CH2:5][C@@H:6]([CH3:8])[O:7][C@@H:2]([CH3:1])[CH2:3]1)[N:17]=2

参加物

5

反応物 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 178461553HCID 178461553、化合物

生成物 1

HCID 178461551HCID 178461551、化合物収率 34%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-((2S,6R)-2,6-dimethyl-morpholin-4-yl)-6-morpholin-4-yl-9H-purine (860 mg, 2.70 mmol) in CH2Cl2 (5 mL) was added bromine (0.04 mL, 3.24 mmol). The mixture was stirred at ambient temperature for 3 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/Heptane gradient) to furnish product as an off-white solid (362.1 mg, 34%). LC/MS analysis using method 7, mass (ES+) m/z 399.1 1HNMR (CDCl3): 4.31 (2H, d), 4.09 (4H, brs), 3.74 (4H, m), 3.59 (2H, m), 2.51 (2H, m), 1.18 (6H, d).

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/Heptane gradient)

出典と根拠

ORDレコード
ord-a9c8ab7ec9df4d71a66454312e5dee87
出典データセット
uspto-grants-2015_03
特許番号
US08987257B2

反応ノート

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