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

HRID 2278542Notes

Reaction equation

HRID 2278542 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)[C:15]([CH3:23])([CH3:22])[CH2:14]2)=[O:12])[N:3]=1.C(#N)C.[I-].[K+].C[Si](C)(C)Cl>O>[Cl:1][C:2]1[N:3]=[C:4]([CH2:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH3:22])([CH3:23])[CH2:14]2)=[O:12])[NH:5][C:6](=[O:8])[CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 866992712-(4-Chloro-6-methoxypyrimidin-2-yl)-1-(3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone

Product 1

HCID 1363786786-Chloro-2-[2-(3,3-dimethyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-3H-pyrimidin-4-oneYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

106 mg of 2-(4-chloro-6-methoxypyrimidin-2-yl)-1-(3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone and 4 ml of acetonitrile are placed in a reactor suitable for microwave irradiation and then 0.45 g of potassium iodide and 347 μl of trimethylchlorosilane are added. The orangey-colored heterogeneous solution is stirred and irradiated at 100° C. for 1 hour. The resulting product is taken up in 25 ml of water and stirred, extraction is carried out with 3 times approximately 25 ml of EtOAc, washing is carried out with 25 ml of saturated NaCl solution, drying is carried out over MgSO4, filtered through a VF filter and the resulting product is concentrated under vacuum. The compound obtained is chromatographed on silica gel, elution being carried out with methanol/dichloromethane (2.5/97.5). The fractions containing the expected compound are combined and evaporated under reduced pressure. 6-Chloro-2-[2-(3,3-dimethyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-3H-pyrimidin-4-one is isolated and characterized: 0.20 g in the form of a yellow solid; yield 70% (LCMS ES+ retention time Tr (min)=1.19; [M+H]+: m/z 318).

Workup

  1. customirradiated at 100° C. for 1 hour
  2. stirringstirred
  3. extractionextraction
  4. washwashing
  5. customdrying
  6. filtrationfiltered through a VF
  7. filtrationfilter
  8. concentrationthe resulting product is concentrated under vacuum
  9. customThe compound obtained
  10. customis chromatographed on silica gel, elution
  11. additionThe fractions containing the expected compound
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d5aba0e7c30e41ac822bb5b79ff0a1e7
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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