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

HRID 2212920Notes

Reaction equation

HRID 2212920 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-96b34185fc334bf59df533b8430e25b7
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

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