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Acetonitrile → 2-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-chloro-3H-pyrimidin-4-one

HRID 2278532
Notes
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Reaction equation

HRID 2278532 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:22])[CH2:12][C:13]1[N:18]=[C:17]([O:19]C)[CH:16]=[C:15]([Cl:21])[N:14]=1.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:22])[CH2:12][C:13]1[NH:18][C:17](=[O:19])[CH:16]=[C:15]([Cl:21])[N:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 866992651-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-chloropyrimidin-2-yl)ethanone

Product 1

HCID 1363786742-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-chloro-3H-pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

2 g of 1-(4-fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-chloropyrimidin-2-yl)ethanone are added to a microwave tube with 30 ml of acetonitrile. 3.1 g of KI and 2.4 ml of trimethylchlorosilane are added. After microwave irradiation for one hour at a temperature of 100° C., the reaction medium is diluted with 100 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 purified on a silica column, eluent: 95/05 dichloromethane/methanol, so as to give 1.13 of 2-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-chloro-3H-pyrimidin-4-one in the form of a white solid.

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. customis purified on a silica column, eluent

Sources & evidence

ORD record
ord-67ad6c9ab5c543989f112d885a17884c
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133168B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes