Trimethylsilyl cyanide → HCID 87111599, compound

HRID 472817Notes

Reaction equation

HRID 472817 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:5]2[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:19]=[C:4]2[N:3]=1.[Si]([C:30]#[N:31])(C)(C)C>C(Cl)Cl.[I-].[Zn+2].[I-]>[OH:9][CH:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]2[N:5]([N:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:19]=2)[C:6]=1[C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[C:30]#[N:31]

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 86670266HCID 86670266, compound

Product 1

HCID 87111599HCID 87111599, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-methyl-2-phenyl-7-p-tolylpyrazolo[1,5-a]pyrimidine-6-carbaldehyde (30 mg, 0.092 mmol) in CH2Cl2 (2 mL) at 0° C. was added zinc iodide (14.63 mg, 0.046 mmol) followed by TMS-CN (0.049 mL, 0.367 mmol). The reaction mixture was stirred at room temperature for 4 h and diluted with CH2Cl2 (100 ml), washed with water, and dried over Na2SO4. The solvent was evaporated and the residue was purified by preparative HPLC to give the title compound (15 mg, 46.2%) as TFA salt. Preparative HPLC condition: Phenomenex Luna C18 30×100 mm S10, 40 to 100% B over 22 minute gradient, 7 minute hold time, A=10% methanol 90% water 0.1% TFA, B=90% methanol 10% water 0.1% TFA. Flow rate: 40 ml/min. 1H-NMR (500 MHz, CDCl3) δ ppm 2.46 (3H, s), 2.89 (3H, s), 5.39 (1H, s), 6.85 (1H, s), 7.16-7.25 (3H, m), 7.30-7.44 (4H, m), 7.63-7.76 (2H, m).

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. customThe solvent was evaporated
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c494f93ad30e4958bdb0a4645a6ac017
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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