Sodium Iodide → HCID 178448671, compound

HRID 621472Notes

Reaction equation

HRID 621472 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[C:16]2[NH:17][N:18]=[C:19]([NH:20][CH3:21])[C:15]=2[C:14](=[O:22])[N:13]([CH2:23][CH2:24][CH2:25][CH3:26])[C:12]1=[O:27])C1C=CC=CC=1.[I-].[Na+].C[Si](Cl)(C)C>C(#N)C>[CH2:23]([N:13]1[C:14](=[O:22])[C:15]2[C:19]([NH:20][CH3:21])=[N:18][NH:17][C:16]=2[N:11]([CH2:10][CH2:9][OH:8])[C:12]1=[O:27])[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 178448672HCID 178448672, compound

Product 1

HCID 178448671HCID 178448671, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 7-(2-benzyloxyethyl)-5-butyl-3-methylaminopyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (1.0 g, 2.7 mM) and sodium iodide (3 g, 20 mM) in acetonitrile (20 ml) was added dropwise trimethylsilyl chloride (2.6 g, 20 mM) at room temperature. The mixture was stirred at room temperature for 2 hours and poured onto ice-water to give crystals. Recrystallization from DMF/methanol/water gave pale yellow crystals (0.3 g, 40%), m.p. 248°-253° C.

Workup

  1. additionpoured onto ice-water
  2. customto give crystals
  3. customRecrystallization from DMF/methanol/water

Sources & evidence

ORD record
ord-e367f9464fe7494caf06bc20fd22c5e5
Source dataset
uspto-grants-1989_04
Patent number
US04824848

Reaction notes

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