Chlorosuccinimide → HCID 68282347, compound

HRID 530175Notes

Reaction equation

HRID 530175 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]2([CH3:20])[OH:13])=[C:4]([O:21][CH3:22])[N:3]=1.C1C(=O)N([Cl:30])C(=O)C1>C1COCC1>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([Cl:30])[N:8]2[C@H:11]2[C@:12]([CH3:20])([OH:13])[C@H:14]([OH:15])[C@@H:16]([CH2:18][OH:19])[O:17]2)=[C:4]([O:21][CH3:22])[N:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 49862756HCID 49862756, compound

Product 1

HCID 68282347HCID 68282347, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

2-Amino-6-methoxy-9-(2-C-methyl-β-D-ribofuranosyl)purine (250 mg, 0.80 mmol) was suspended in dry THF (10 mL) and 1 mol eq. of NCS (110 mg, 0.80 mmol) was added. The mixture was warmed to 35° C. and stirred in the dark overnight. After that time, solution was concentrated and the resulting solid was purified by silica gel chromatography using 1-4% (gradient) of MeOH in chloroform to yield 235 mg (85% yield) of the desired product.

Workup

  1. concentrationAfter that time, solution was concentrated
  2. customthe resulting solid was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a6bba392cd90427bb3c469309f0b6c4c
Source dataset
uspto-grants-2016_05
Patent number
US09351989B2

Reaction notes

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