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

HRID 1836244Notes

Reaction equation

HRID 1836244 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.[Cl:21]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:10]([Cl: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 31398ChlorosuccinimideHCID 30118937-Deaza-2'-C-methyladenosine

Product 1

HCID 30118985-Chloro-7-(2-C-methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a pre-cooled solution (0° C.) of the compound from Step F of Example 62 (140 mg, 0.50 mmol) in DMF (2.5 mL) was added N-chlorosuccinimide (0.075 g, 0.55 mmol) in DMF (0.5 mL) dropwise. The solution was stirred at rt for 1 h and the reaction 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 (55 mg) as a colorless solid.

Workup

  1. customthe reaction quenched by addition of methanol (4 mL)
  2. customevaporated in vacuo
  3. customThe crude product was purified on silica gel
  4. additionFractions containing the product
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4753ca719d2f4ec9ad466285820b30ca
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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