Methyl iodide → HCID 58111179, compound

HRID 2194419Notes

Reaction equation

HRID 2194419 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:22])[N:13]([C:15]3[N:20]=[CH:19][NH:18][C:17](=[O:21])[CH:16]=3)[CH:14]=2)[CH:5]=[CH:4][N:3]=1.CI.[C:25](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:22])[N:13]([C:15]3[N:20]=[CH:19][N:18]([CH3:25])[C:17](=[O:21])[CH:16]=3)[CH:14]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136395140HCID 136395140, compound

Product 1

HCID 58111179HCID 58111179, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 50.0 mg (0.160 mmol) of 6-[4-(2-chloro-pyridin-4-ylethynyl)-2-methyl-imidazol-1-yl]-3H-pyrimidin-4-one and 0.020 ml (45.5 mg, 0.321 mmol) of methyl iodide in 10 ml of acetone were added 44 mg (0.321 mmol) of potassium carbonate. The suspension was stirred for 48 at room temperature. The suspension was filtered and the salts were washed with acetone. The filtrate was concentrated in vaccuo. The residue was dissolved in ethyl acetate/methanol, 1 g of silicagel was added and the suspension was concentrated in vaccuo. The silicagel containing adsorbed product was loaded onto a flash chromatography column and eluted with a 90:10 mixture of ethyl acetate and methanol. One obtains 6 mg (0.018 mmol, 11.5%) of the title compound as a crystalline light yellow solid, MS: 326.2, 328.2 (M+H+) separated from the undesired O-alkylation product.

Workup

  1. filtrationThe suspension was filtered
  2. washthe salts were washed with acetone
  3. concentrationThe filtrate was concentrated in vaccuo
  4. dissolutionThe residue was dissolved in ethyl acetate/methanol
  5. addition1 g of silicagel was added
  6. concentrationthe suspension was concentrated in vaccuo
  7. additionThe silicagel containing adsorbed product
  8. washeluted with a 90:10 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-7f0fbd0195764ae98586097293f33154
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Reaction notes

Loading…