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

HRID 1982554

Reaktionsgleichung

Reaktionsgleichung von HRID 1982554
[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. 1H NMR (CDCl3): δ 5.92 (CH2), 6.8-7.4 (Ph), 7.80 and 8.43 (H-4 and H-6, respectively, J 3 Hz). IR (KBr): 1660 cm-1 (CO). MS (70 eV, m/z (% rel. int.)): 236 (7, M), 145 (32), 143 (100), 116 (31), 94 (6), 77 (18).

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-fce50a9b3e6a427eb173337aa08412c8
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04596870

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