Chlorosuccinimide → 3-[5-chloro-4-(2,4-difluoro-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl ester

HRID 2172594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172594
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])[N:13]=[C:12]2[CH3:28])[CH:5]=1.[Cl:30]N1C(=O)CCC1=O>C(O)(C)C.ClC(Cl)C(O)=O>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[C:15]([Cl:30])=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])[N:13]=[C:12]2[CH3:28])[CH:5]=1

Komponenten

5

Edukt 2

HCID 31398ChlorosuccinimideHCID 21089018Methyl 3-[4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoate

Produkt 1

HCID 210901983-[5-chloro-4-(2,4-difluoro-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl esterAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6597Dichloroacetic AcidKatalysatorHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3-[4-(2,4-difluoro-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl ester from Example 1, Step A (260 mg, 0.65 mmol) in isopropanol (5 mL) was added N-chlorosuccinimide (95 mg, 0.71 mmol) and 3 drops of dichloroacetic acid. The solution was heated at 60° C. for three hours. The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the chlorinated product as a light yellow semi-solid (230 mg, 82%). MS (M+H): 435

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe slurry was filtered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-015134128ec44ec29500c8eacc47b2ed
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056110B2

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