Potassium Iodide → 2-[1-(4-fluoro-2,3-dihydro-1H-indol-1-yl)-1-oxopropan-2-yl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one

HRID 2278586Notes

Reaction equation

HRID 2278586 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C:11](=[O:28])[CH:12]([C:14]1[N:19]=[C:18]([O:20]C)[CH:17]=[C:16]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:15]=1)[CH3:13].[I-].[K+].C(#N)C.C[Si](C)(C)Cl>C(OCC)(=O)C.O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C:11](=[O:28])[CH:12]([C:14]1[NH:19][C:18](=[O:20])[CH:17]=[C:16]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[N:15]=1)[CH3:13]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 682815811-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)propan-1-one

Product 1

HCID 1363786882-[1-(4-fluoro-2,3-dihydro-1H-indol-1-yl)-1-oxopropan-2-yl]-6-(morpholin-4-yl)pyrimidin-4(3H)-oneYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

210 mg of 1-(4-fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-yl-pyrimidin-2-yl)propan-1-one, 270 mg of potassium iodide, 7 ml of acetonitrile and 208 ml of trimethylchlorosilane are added to a microwave tube. After microwave irradiation for one hour at a temperature of 100° C., the reaction medium is diluted with 20 ml of ethyl acetate and 20 ml of water. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is stirred in the presence of 5 ml of ethyl acetate and 20 ml of petroleum ether. The solid obtained is filtered off and then dried under reduced pressure. 163 mg of 2-[1-(4-fluoro-2,3-dihydro-1H-indol-1-yl)-1-oxopropan-2-yl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are thus obtained in the form of a pale yellow solid, the characteristics of which are the following:

Workup

  1. customAfter microwave irradiation for one hour at a temperature of 100° C.
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customThe solid obtained
  7. filtrationis filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-fbe5718c43fa46b89d833049c0b41425
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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