Sodium Iodide → HCID 136043195, compound

HRID 530173Notes

Reaction equation

HRID 530173 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([I:21])[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:22]C)[N:3]=1.C(N(CC)C(C)C)C.[Na+].[I-].C[Si](Cl)(C)C.C(N(CC)CC)C>C(#N)C>[NH2:1][C:2]1[NH:3][C:4](=[O:22])[C:5]2[N:6]=[C:7]([I:21])[N:8]([C@H:11]3[C@@:12]([OH:13])([CH3:20])[C@H:14]([OH:15])[C@@H:16]([CH2:18][OH:19])[O:17]3)[C:9]=2[N:10]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 521913N,N-Diethyl-2-propanamineHCID 60141156HCID 60141156, compound2×

Product 1

HCID 136043195HCID 136043195, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound can be synthesized from 2-amino-8-iodo-6-methoxy-9-(2-C-methyl-β-D-ribofuranosyl)purine using procedures familiar to one skilled in the art. For example: To a solution of 2-amino-8-iodo-6-methoxy-9-(2-C-methyl-β-D-ribofuranosyl)purine (XV)(1 mmol) in acetonitrile (3.0 mL) under nitrogen is added diethylisopropyl amine (52 mL, 0.3 mmol), followed by the addition of NaI (99 mg, 0.5 mmol) and TMSCl (64 mL, 0.5 mmol). The contents are stirred under nitrogen for 16 h. After completion of the reaction (monitoring by TLC), triethyl amine (30 mL, 0.3 mmol) are added. The reaction is concentrated under vacuum, and the solids are dissolved in methanol/water mixture (1.5 mL, 0.5 mL) and are stirred for 15 min.

Workup

  1. additionare added
  2. concentrationThe reaction is concentrated under vacuum
  3. dissolutionthe solids are dissolved in methanol/water mixture (1.5 mL, 0.5 mL)
  4. stirringare stirred for 15 min.

Sources & evidence

ORD record
ord-7bde98d3fc9d4ed7ad57cc6fc173c695
Source dataset
uspto-grants-2016_05
Patent number
US09351989B2

Reaction notes

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