Sodium Iodide → HCID 178510194, compound

HRID 1500745Notes

Reaction equation

HRID 1500745 reaction equation
Cl[Si](C)(C)C.[I-].[Na+].C[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[CH:17]=[N:18][N:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=23)[N:11]=1>C(#N)C>[OH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[CH:17]=[N:18][N:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=23)[N:11]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 67326673HCID 67326673, compound

Product 1

HCID 178510194HCID 178510194, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Chlorotrimethylsilane (0.61 mL, 4.83 mmol) and sodium iodide (0.72 g, 4.83 mmol) were added to a stirred suspension of 3-(4-methoxypyrimidin-2-yl)pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 3a, 0.14 g, 0.54 mmol) in acetonitrile (11 mL) and the mixture was heated at 70° C. in a sealed tube and left overnight. The mixture was then cooled and the solvent evaporated. Water (4 mL) and 10% aqueous sodium thiosulfate solution (5 mL) were added to the residue and the suspension was stirred for 20 minutes. The suspension was filtered and the precipitate was dried in vacuo to give the title compound in quantitative yield which was used in the next synthetic step without further purification.

Workup

  1. temperatureThe mixture was then cooled
  2. customthe solvent evaporated
  3. additionWater (4 mL) and 10% aqueous sodium thiosulfate solution (5 mL) were added to the residue
  4. filtrationThe suspension was filtered
  5. customthe precipitate was dried in vacuo

Sources & evidence

ORD record
ord-a25590d6400d493292a432ee4fbb587a
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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