Triethylamine → Ethyl 6-(chloromethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate

HRID 1868459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1868459
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=[C:13]2[N:12]=[C:11]([CH3:23])[C:10]=1[CH2:24]O.CS([Cl:30])(=O)=O.CCN(CC)CC>C(Cl)Cl>[Cl:30][CH2:24][C:10]1[C:11]([CH3:23])=[N:12][C:13]2[N:14]([CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)[C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 46901745Ethyl 5-(2,4-dichlorophenyl)-6-(hydroxymethyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate

Produkt 1

HCID 46901746Ethyl 6-(chloromethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylateAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 5-(2,4-dichlorophenyl)-6-(hydroxymethyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate (430 mg, 1.12 mmol) in CH2Cl2 (10 mL) was added MsCl (0.1 mL, 1.35 mmol) and Et3N (0.24 mL, 1.69 mmol). After 10 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The mixture was extracted with H2O and brine before drying over MgSO4. Filtration and concentration under reduced pressure gave ethyl 6-(chloromethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate (448 mg, 100% crude yield) as a yellow oil.

Aufarbeitung

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. extractionThe mixture was extracted with H2O and brine
  4. dry with materialbefore drying over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dd4fc6afb4cc49958b311a34f1b61ba0
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07635699B2

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