Trimethylsilyl iodide → HCID 178481616, compound

HRID 600448Notes

Reaction equation

HRID 600448 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:8]=[C:7]2[C:3]=1[N:4]([CH3:31])[C:5](=[O:30])[N:6]2[C@H:22]1[CH2:27][CH2:26][C@H:25]([O:28]C)[CH2:24][CH2:23]1.I[Si](C)(C)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:8]=[C:7]2[C:3]=1[N:4]([CH3:31])[C:5](=[O:30])[N:6]2[C@H:22]1[CH2:23][CH2:24][C@H:25]([OH:28])[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 178496592HCID 178496592, compound

Product 1

HCID 178481616HCID 178481616, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an oven dried flask under Argon flow was added 3-(6-chloro-9-(trans-4-methoxycyclohexyl)-7-methyl-8-oxo-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile (0.55 g, 1.25 mmol) in chloroform, followed by iodotrimethylsilane (0.1 mL, 1.25 mmol, 1 equiv.) The reaction mixture was stirred at room temperature for 4 h. Upon completion (HPLC monitoring), the reaction was slowly quenched with water. The organic layer was separated and the aqueous layer extracted with CHCl3 (15 ml×3) and with EtOAc (15 mL×3). The combined organic layers were dried (MgSO4), and concentrated in vacuo to give a dark solid (66% crude yield). MS (EI) m/z 424 (MH)+.

Workup

  1. customTo an oven dried flask under Argon flow
  2. customUpon completion (HPLC monitoring), the reaction was slowly quenched with water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with CHCl3 (15 ml×3) and with EtOAc (15 mL×3)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a dark solid (66% crude yield)

Sources & evidence

ORD record
ord-2a897d4e3dd24e6e8402315ec7c974d1
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

Loading…