N-bromobutanimide → 5-Bromo-7-(2-C-methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2252673Notes

Reaction equation

HRID 2252673 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[Br:21]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:10]([Br:21])=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 30118937-Deaza-2'-C-methyladenosine

Product 1

HCID 30118995-Bromo-7-(2-C-methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a pre-cooled solution (0° C.) of the compound from Step F of Example 2 (28 mg, 0.10 mmol) in DMF (0.5 mL) was added N-bromosuccinimide (0.018 g, 0.10 mmol) in DMF (0.5 mL) dropwise. The solution was stirred at 0° C. for 20 min, then at room temperature for 10 min. The reaction was quenched by addition of methanol (4 mL) and evaporated in vacuo. The crude product was purified on silica gel using methanol/dichloromethane (1:9) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (13.0 mg) as a colorless solid.

Workup

  1. waitat room temperature for 10 min
  2. customThe reaction was quenched by addition of methanol (4 mL)
  3. customevaporated in vacuo
  4. customThe crude product was purified on silica gel
  5. additionFractions containing the product
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-6a4f1edc340d4fd39fd7725eb7239b93
Source dataset
uspto-grants-2008_01
Patent number
US07323453B2

Reaction notes

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