Triethylamine → 1-(3-Methylphenylthio)methyl-5-fluoropyrimidin-2-one

HRID 247080

Reaktionsgleichung

Reaktionsgleichung von HRID 247080
Cl[CH2:2][S:3][C:4]1[CH:5]=[C:6]([CH3:10])[CH:7]=[CH:8][CH:9]=1.[F:11][C:12]1[CH:13]=[N:14][C:15](=[O:18])[NH:16][CH:17]=1.C(N(CC)CC)C.[K+].[Br-]>ClCCl>[CH3:10][C:6]1[CH:5]=[C:4]([S:3][CH2:2][N:16]2[CH:17]=[C:12]([F:11])[CH:13]=[N:14][C:15]2=[O:18])[CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 1014985-Fluoropyrimidin-2-oneHCID 253877Potassium BromideHCID 128408943-Methylphenyl chloromethyl sulfide

Produkt 1

HCID 156505001-(3-Methylphenylthio)methyl-5-fluoropyrimidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(Chloromethylthio)toluene (6.5 mmol) was added to a solution of 5-fluoropyrimidin-2-one (6.5 mmol) and triethylamine (6.5 mmol) in dichloromethane (75 ml) and the resultant mixture heated under reflux for 2 days. The solvent was then distilled off, the residue triturated with water and the residual material extracted with CCl4. Evaporation of the extracts and crystallisation of the residue from ethyl acetate gave the pure product; 0.40 g (25%), m.p. 124° C. (Found: C57.42; H4.63. Calc. for C12H11FN2OS: C57.59; H4.43) 1H NMR (DMSO d6); δ 2.28 (Me), 5.17(CH2), 7.2 (Ph), 8.05 (H-4), 8.70 (H-6). IR (KBr): 1670 cm-1 (CO), MS [70 eV, m/z (% rel. int.)]: 250 (8,M), 137(11), 136(36), 135(10), 128(7), 127(100), 100(34), 91(9).

Aufarbeitung

  1. temperatureunder reflux for 2 days
  2. distillationThe solvent was then distilled off
  3. customthe residue triturated with water
  4. extractionthe residual material extracted with CCl4
  5. customEvaporation of the extracts and crystallisation of the residue from ethyl acetate
  6. customgave the pure product

Quellen und Nachweise

ORD-Eintrag
ord-be950a6fa23d444c879577fb33e2a1e5
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705791

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