5-Chloro-2(1H)-pyrimidinone → 5-Chloro-1-(3-furoylmethyl)pyrimidin-2-one

HRID 1906150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1906150
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[CH:17]=[CH:16][O:15][CH:14]=1)=[O:12]>C(N(CC)CC)C.C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11]([C:13]2[CH:17]=[CH:16][O:15][CH:14]=2)=[O:12])[CH:7]=1

Komponenten

5

Edukt 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 186125513-Bromoacetylfuran

Produkt 1

HCID 127912445-Chloro-1-(3-furoylmethyl)pyrimidin-2-oneAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 5-chloropyrimidin-2-one (587 mg) and crude 3-bromoacetylfuran (2.00 g, ca. 4.5 mmol, based on purity ca. 40% by 1H n.m.r; contaminated with 3-dibromoacetylfuran and diethyl ether) in triethylamine (0.95 ml) and ethanol (25 ml) was stirred at room temperature. After 45 min with solvent was removed and the residue triturated with ethyl acetate. The resulting solid was collected and retriturated with water. This gave a buff solid which was crystallised from ethyl acetate to give the title pyrimidinone (335 mg), m.p. 195°-197° C. (dec), λmax (EtOH) 333 nm (ε 2,530).

Aufarbeitung

  1. customAfter 45 min with solvent was removed
  2. customthe residue triturated with ethyl acetate
  3. customThe resulting solid was collected
  4. customretriturated with water
  5. customThis gave a buff solid which
  6. customwas crystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6e8a7b94c0684666a0c46504021d0e00
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04650800

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