Acetonitrile → 2-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-chloro-3H-pyrimidin-4-one
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]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- customAfter microwave irradiation for one hour at a temperature of 100° C.
- dry with materialthe organic phase is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue obtained
- customis purified on a silica column, eluent
Sources & evidence
- ORD record
- ord-67ad6c9ab5c543989f112d885a17884c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133168B2
Reaction notes
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