Trimethylsilyl iodide → HCID 24856097, compound

HRID 2361085Notes

Reaction equation

HRID 2361085 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH:17][C:18]3[CH:55]=[CH:54][C:21]([O:22][C:23]4[C:28]([C:29]5[CH:34]=[CH:33][N:32]=[C:31]([NH:35][P:36](=[O:53])([O:45]CC6C=CC=CC=6)[O:37]CC6C=CC=CC=6)[N:30]=5)=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:20][CH:19]=3)=[N:9][N:8]=2)[S:5][CH:6]=1.C(#N)C.C(Cl)Cl.[I:62][Si](C)(C)C>CO>[IH:62].[IH:62].[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH:17][C:18]3[CH:55]=[CH:54][C:21]([O:22][C:23]4[C:28]([C:29]5[CH:34]=[CH:33][N:32]=[C:31]([NH:35][P:36](=[O:37])([OH:45])[OH:53])[N:30]=5)=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:20][CH:19]=3)=[N:9][N:8]=2)[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 21877088Acetonitrile methylene chlorideHCID 66731808HCID 66731808, compound

Product 1

HCID 24856097HCID 24856097, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slightly cloudy mixture of dibenzyl 4-(2-(4-(4-(4-methylthiazol-2-yl)phthalazin-1-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-ylphosphoramidate (0.086 g, 0.11 mmol) in 3 mL 5:1 ACN/DCM was added iodotrimethylsilane (0.16 ml, 1.1 mmol) dropwise via syringe at ambient temperature under nitrogen. After 5 min, 0.6 mL MeOH was added and the stir bar was removed. The reaction was concentrated in vacuo and suspended in DCM and filtered. The resulting orange solid was collected and dried in vacuo to provide

Workup

  1. customthe stir bar was removed
  2. concentrationThe reaction was concentrated in vacuo
  3. filtrationfiltered
  4. customThe resulting orange solid was collected
  5. customdried in vacuo
  6. customto provide

Sources & evidence

ORD record
ord-20329a34013841c3bddf7389567d5dbc
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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