Chlorosuccinimide → 7-(2'-C-methyl-beta-D-ribofuranosyl)-5-chloro-4-hydroxylamino pyrrolo[2,3-d]pyrimidine

HRID 30963Notes

Reaction equation

HRID 30963 reaction equation
[CH3:1][C@@:2]1([OH:21])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH:19][OH:20])[C:13]=2[CH:12]=[CH:11]1.C1C(=O)N([Cl:29])C(=O)C1>CN(C=O)C>[CH3:1][C@@:2]1([OH:21])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH:19][OH:20])[C:13]=2[C:12]([Cl:29])=[CH:11]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 102665497-(2'-C-methyl-beta-D-ribofuranosyl)-4-hydroxylamino-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 102461047-(2'-C-methyl-beta-D-ribofuranosyl)-5-chloro-4-hydroxylamino pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Nucleoside 117 (0.1 mmol) is dissolved in DMF (0.5 mL) and cooled to 0° C. NCS (0.1 mmol) dissolved in DMF (0.5 mL) is then added dropwise and the reaction stirred for 30 minutes at 0° C. and 30 minutes at room temperature. The reaction is quenched with methanol (5 mL) and then concentrated. Column chromatography (SiO2) with MeOH/DCM affords 123.

Workup

  1. additionis then added dropwise
  2. customThe reaction is quenched with methanol (5 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-75161279d5f446eca4ddbf1e9bf8f6b3
Source dataset
uspto-grants-2008_09
Patent number
US07425547B2

Reaction notes

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