N-bromobutanimide → HCID 23518344, compound

HRID 1836265Notes

Reaction equation

HRID 1836265 reaction equation
[CH3:1][C@@:2]1([OH:20])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:19]2[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=2[N:12]=[CH:11]1.[Br:21]N1C(=O)CCC1=O>CN(C=O)C>[Br:21][C:11]1[N:10]([C:19]2[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=2[N:12]=1)[C@@H:3]1[O:4][C@H:5]([CH2:8][OH:9])[C@@H:6]([OH:7])[C@@:2]1([CH3:1])[OH:20]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5009002'-C-methyladenosine

Product 1

HCID 23518344HCID 23518344, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′-C-methyladenosine [for preparation, see J. Med. Chem. 41:1708 (1998)] (138 mg, 0.5 mmol) in DMF (4 mL) was added N-bromosuccinimide (231 mg, 1.35 mmol). The solution was stirred protected from light at rt for 2 d and then evaporated in vacuo. The crude product was purified on a silica gel column (3×9 cm) using dichloromethane/methanol (25/1, 20/1 and 15/1) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (38 mg) as a white solid.

Workup

  1. customevaporated in vacuo
  2. customThe crude product was purified on a silica gel column (3×9 cm)
  3. additionFractions containing the product
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-73d92e9bf1b44f27b1322c66a8a31c11
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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