Triethylamine → 5-Chloro-1-(phenoxymethyl)pyrimidin-2(1H)-one

HRID 247067

Reaktionsgleichung

Reaktionsgleichung von HRID 247067
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.C(N(CC)CC)C.Cl[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[O:18]([CH2:17][N:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[N:6][C:5]1=[O:8])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 81201(Chloromethoxy)benzeneHCID 1085785-Chloro-2(1H)-pyrimidinone

Produkt 1

HCID 130629345-Chloro-1-(phenoxymethyl)pyrimidin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

5-Chloropyrimidin-2-one (5 mmol) and triethylamine (5 mmol) were stirred together in dichloromethane (50 ml). When all the solid had dissolved a solution of chloromethoxybenzene (see Preparation 2) (5 mmol) in dichloromethane (25 ml) was added with stirring at room temperature. The resultant mixture was stirred for 24 h at this temperature before the solvent was distilled off. The residue was triturated with water (30 ml), extracted into chloroform (3×20 ml), and the dried (MgSO4) solution evaporated to yield a mixture of the title compound and the O-alkylated isomer in the ratio 3:1; yield 7.00 g (85%). The N-isomer was separated by column chromatography on silica gel; m.p. 146° C.

Aufarbeitung

  1. additionwas added
  2. distillationwas distilled off
  3. customThe residue was triturated with water (30 ml)
  4. extractionextracted into chloroform (3×20 ml)
  5. dry with materialthe dried (MgSO4) solution
  6. customevaporated
  7. customto yield

Quellen und Nachweise

ORD-Eintrag
ord-4ac491f287534f00a08017e4a638c2b1
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705791

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