Sodium Carbonate → 5-Chloro-1-(3-thienylmethyl)pyrimidin-2-one

HRID 434643

Reaktionsgleichung

Reaktionsgleichung von HRID 434643
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.Br[CH2:11][C:12]1[CH:16]=[CH:15][S:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C)C=O.O>[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[N:7]([CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:8]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 5207033-(Bromomethyl)thiopheneHCID 126485235-Chloropyrimidin-2-ol hydrochloride

Produkt 1

HCID 204917595-Chloro-1-(3-thienylmethyl)pyrimidin-2-oneAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-chloropyrimidin-2-one hydrochloride (502 mg), 3-bromomethylthiophene (1.069 g), anhydrous sodium carbonate (955 mg) and benzyltrimethylammonium chloride (12 mg) in dry N,N-dimethylformamide (15 ml) was stirred at room temperature. After 22 h the reaction mixture was diluted with water (120 ml) and the resulting precipitate was collected, washed with water and dried to give a pale yellow solid (233 mg). The solid was crystallised from ethanol to give white crystals of the title thiophene (184 mg), m.p. 194°-195° C., λmax 229 nm (ε 14,410), 233 nm (ε 3,080), λinf 246 nm (ε 5,210).

Aufarbeitung

  1. customthe resulting precipitate was collected
  2. washwashed with water
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2b8a98689de64f6a9cfeb696e26be292
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04399140

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