Potassium trimethylsilanolate → HCID 71153301, compound

HRID 872248Notes

Reaction equation

HRID 872248 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[C:13]([C:15]([O:17]C)=[O:16])[N:12]=[CH:11][N:10]3[CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[O-].[K+]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[N:12]=[CH:11][N:10]3[CH:19]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 71153182HCID 71153182, compound

Product 1

HCID 71153301HCID 71153301, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100 mL round bottom flask was charged with methyl 2-phenylimidazo[1,2-c]pyrimidine-7-carboxylate (500 mg, 1.97 mmol) and dissolved in THF (19.70 mL) using sonication. To that stirring solution was added potassium trimethylsilanolate (760 mg, 5.92 mmol). After 30 minutes, TLC showed complete consumption of the starting material. LCMS showed complete consumption of starting material and the formation of a large, more polar peak consistent with the desired product by mass (m/z=240 [M+H]+/Methanol/Water/Ammonium Acetate Phenomenex Luna C18, 30×2 mm, 3μ ES+/−). The mixture was quenched using 10 mL of 4.0M HCl in dioxane. The now yellow slurry was concentrated under reduced pressure. To remove any residual water, 50 mL of acetonitrile was added and the solution was concentrated under reduced pressure. The resulting yellow solid was taken on without any further characterization or purification. Mass found 240 [M+H]+.

Workup

  1. customsonication
  2. customconsumption of the starting material
  3. customconsumption of starting material
  4. customThe mixture was quenched
  5. concentrationThe now yellow slurry was concentrated under reduced pressure
  6. customTo remove any residual water, 50 mL of acetonitrile
  7. additionwas added
  8. concentrationthe solution was concentrated under reduced pressure
  9. customThe resulting yellow solid was taken on without any further characterization or purification

Sources & evidence

ORD record
ord-9a41ebdb24f1454a9731e9547cbf00c8
Source dataset
uspto-grants-2015_03
Patent number
US08975276B2

Reaction notes

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