N-bromobutanimide → HCID 68282408, compound

HRID 530174Notes

Reaction equation

HRID 530174 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]2([CH3:20])[OH:13])=[C:4]([O:21][CH3:22])[N:3]=1.C1C(=O)N([Br:30])C(=O)C1>CO>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([Br:30])[N:8]2[C@H:11]2[C@:12]([CH3:20])([OH:13])[C@H:14]([OH:15])[C@@H:16]([CH2:18][OH:19])[O:17]2)=[C:4]([O:21][CH3:22])[N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 49862756HCID 49862756, compound

Product 1

HCID 68282408HCID 68282408, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Amino-6-methoxy-9-(2-C-methyl-β-D-ribofuranosyl)purine (1.5 g, 4.82 mmol) was suspended in MeOH (50 mL) and 1 mol eq. of NBS (1.03 g, 4.82 mmol) was added. The mixture was stirred at room temperature for 4 h. After that time, solution was concentrated and the resulting solid was purified by silica gel chromatography using 1-4% (gradient) of MeOH in chloroform to yield 1.65 g (88% yield) of the desired product.

Workup

  1. concentrationAfter that time, solution was concentrated
  2. customthe resulting solid was purified by silica gel chromatography

Sources & evidence

ORD record
ord-06930dd165e74c8a92d08842ef7e83e4
Source dataset
uspto-grants-2016_05
Patent number
US09351989B2

Reaction notes

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