Sodium Iodide → HCID 178502687, compound

HRID 1406017Notes

Reaction equation

HRID 1406017 reaction equation
[CH3:1][O:2][N:3]([CH3:23])[C:4]([C:6]1[C:10]2[CH2:11][CH2:12][CH2:13][C:14]3[C:15](=[N:16][C:17]([O:20]C)=[N:18][CH:19]=3)[C:9]=2[N:8]([CH3:22])[N:7]=1)=[O:5].[I-].[Na+].C[Si](Cl)(C)C>CC#N>[OH:20][C:17]1[N:16]=[C:15]2[C:9]3[N:8]([CH3:22])[N:7]=[C:6]([C:4]([N:3]([O:2][CH3:1])[CH3:23])=[O:5])[C:10]=3[CH2:11][CH2:12][CH2:13][C:14]2=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 86701834HCID 86701834, compound

Product 1

HCID 178502687HCID 178502687, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N,9-dimethoxy-N,1-dimethyl-1,4,5,6-tetrahydropyrazolo[4′,3′:6,7]cyclohepta[1,2-d]pyrimidine-3-carboxamide (583 mg, 1.8 mmol) in CH3CN (35 mL), sodium iodide (550 mg, 3.67 mmol) and trimethylsilylchloride (0.525 mL, 4.14 mmol) were added in sequence. Mixture was stirred for 24 h under argon atmosphere at room temperature then a second portion of sodium iodide (275 mg, 1.8 mmol) and trimethylsilylchloride (0.276 mL, 2.1 mmol) were added in sequence. After 24 h the solvent was evaporated, the residue dissolved with a mixture of DCM/MeOH (4/1) and washed with a saturated aqueous solution of Na2S2O3. The organic layer was dried over Na2SO4. The residue was crystallized from MeOH to give 452 mg (83% yield) of a white solid.

Workup

  1. customAfter 24 h the solvent was evaporated
  2. dissolutionthe residue dissolved with a mixture of DCM/MeOH (4/1)
  3. washwashed with a saturated aqueous solution of Na2S2O3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-73cbd6e4b42d41548f3bf47b16536875
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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