Chlorosuccinimide → HCID 15817630, compound

HRID 1611435Notes

Reaction equation

HRID 1611435 reaction equation
[Cl:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:11]=[C:12]([O:33][CH3:34])[C:13]2[CH:18]=[CH:17][N:16]([C@@H:19]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[CH2:20]3)[C:14]=2[N:15]=1>ClCCl>[NH2:9][C:10]1[N:11]=[C:12]([O:33][CH3:34])[C:13]2[CH:18]=[C:17]([Cl:1])[N:16]([C@@H:19]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[CH2:20]3)[C:14]=2[N:15]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 15817629HCID 15817629, compound

Product 1

HCID 15817630HCID 15817630, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

36.6 mg (0.27 mmol) of N-chlorosuccinimide are added to a solution of 50 mg (0.14 mmol) of 2-amino-7-(2-deoxy-3,5-di-O-acetyl-β-D-erythropentofuranosyl)-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine in 3 ml of dichloromethane, and the mixture is stirred at room temperature for 12 h. The solvent is stripped off and the residue is chromatographed on silica gel in CH2Cl2/acetone (9:1). 30 mg (54%) of a colorless foam are obtained from the slowly migrating main zone.

Workup

  1. customthe residue is chromatographed on silica gel in CH2Cl2/acetone (9:1)

Sources & evidence

ORD record
ord-5e0dd5c997584e5c80ead680cb332471
Source dataset
uspto-grants-2006_01
Patent number
US06987177B2

Reaction notes

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