Trimethylsilyl iodide → HCID 24856097, compound

HRID 593994Notes

Reaction equation

HRID 593994 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 4-(2-(4-(4-(4-methylthiazol-2-yl)phthalazin-1-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-ylphosphoramidic acid dihydroiodide as an orange solid. MS m/z=585 [M+H]+. Calculated for C27H21N8O4PS: 584.6.

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

Sources & evidence

ORD record
ord-e17d3d5b271349f39232d5cdd7a5dc33
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Reaction notes

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