Triethylamine → 1-(4-Chlorophenoxy)methyl-5-iodopyrimidin-2-one

HRID 247068

Reaktionsgleichung

Reaktionsgleichung von HRID 247068
Cl[CH2:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[I:11][C:12]1[CH:13]=[N:14][C:15](=[O:18])[NH:16][CH:17]=1.C(N(CC)CC)C>ClCCl>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:2][N:16]2[CH:17]=[C:12]([I:11])[CH:13]=[N:14][C:15]2=[O:18])=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 88801alpha,4-DichloroanisoleHCID 119590965-Iodopyrimidin-2-ol

Produkt 1

HCID 130629381-(4-Chlorophenoxy)methyl-5-iodopyrimidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

The title compound was prepared in a manner similar to that described in Example 6, by adding a solution of 1-chloromethoxy-4-chlorobenzene (see Preparation 3) (10 mmol) in dichloromethane (10 ml) to a solution of 5-iodopyrimidin-2-one (10 mmol) and triethylamine (10 mmol) in dichloromethane (50 ml), and heating the resultant mixture under reflux for 3 h. The product, 2.05 g (56%), consisted of the N- and O-isomers in the ratio 4:1. The O-isomer was removed from the product by extraction with acetone and the remaining N-isomer was recrystallized from EtOAc; m.p. 216° C. (Found C36.64; H2.24 Calc. for C11H8ClIN2O2 : C36 44; H2.23) 1H NMR (DMSO-d6 /CDCl3): δ 5.85 (CH2), 6.9-7.5 (Ph), 8.68 and 8.82 (H-4 and H-6, respectively, J 3 Hz). IR (KBr) 1650 cm-1 (CO). MS (70 eV, m/z (% rel. int.)): 362 (37,M) 235 (100), 222 (6), 108 (22).

Aufarbeitung

  1. temperatureunder reflux for 3 h
  2. customThe O-isomer was removed from the product by extraction with acetone
  3. customthe remaining N-isomer was recrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-3883545105944154b5e99e30340704d3
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705791

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