Potassium Iodide → 6-chloro-2-[2-(2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-5H-pyrimidin-4-one

HRID 2278544Notes

Reaction equation

HRID 2278544 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[N:5]=[C:4]([CH2:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH:14]2[CH3:22])=[O:12])[N:3]=1.[I-].[K+].C[Si](C)(C)Cl>C(#N)C.O>[Cl:1][C:2]1[CH2:7][C:6](=[O:8])[N:5]=[C:4]([CH2:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH:14]2[CH3:22])=[O:12])[N:3]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 866992722-(4-Chloro-6-methoxypyrimidin-2-yl)-1-(2-methyl-2,3-dihydroindol-1-yl)ethanone

Product 1

HCID 682817676-chloro-2-[2-(2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-5H-pyrimidin-4-oneYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

In a reactor suitable for microwave irradiation, 1.3 g of 2-(4-chloro-6-methoxypyrimidin-2-yl)-1-(2-methyl-2,3-dihydroindol-1-yl)ethanone are placed in 20 ml of acetonitrile, 2 g of potassium iodide and 1.7 ml of trimethylchlorosilane. The heterogeneous solution is stirred while microwave-heating at 100° C. for 90 minutes. The resulting product is taken up in 25 ml of water, extraction is carried out with ethyl acetate, washing is carried out with 25 ml of saturated NaCl solution, drying is carried out over MgSO4, filtration is carried out through a VF filter and the resulting product is concentrated under vacuum. The compound obtained is chromatographed on silica gel (40-63 μm), elution being carried out with a mixture of dichloromethane and methanol (90/10, v/v). The fractions containing the expected compound are combined and evaporated. The compound obtained is triturated from a mixture of ethyl acetate and diisopropyl ether, filtered and dried at ambient temperature (20° C.). 6-Chloro-2-[2-(2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-5H-pyrimidin-4-one is isolated in the form of a beige solid (2.2 g), yield 89%.

Workup

  1. extractionextraction
  2. washwashing
  3. customdrying
  4. filtrationis carried out over MgSO4, filtration
  5. filtrationfilter
  6. concentrationthe resulting product is concentrated under vacuum
  7. customThe compound obtained
  8. customis chromatographed on silica gel (40-63 μm), elution
  9. additionbeing carried out with a mixture of dichloromethane and methanol (90/10
  10. additionThe fractions containing the expected compound
  11. customevaporated
  12. customThe compound obtained
  13. customis triturated from a mixture of ethyl acetate and diisopropyl ether
  14. filtrationfiltered
  15. customdried at ambient temperature (20° C.)

Sources & evidence

ORD record
ord-6325728c591c46f1aae3f11bf4814d65
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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