Dimethoxymethane → 3-methoxymethyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone

HRID 1455

Reaktionsgleichung

Reaktionsgleichung von HRID 1455
[C:1]1([C:7]2[NH:12][C:11](=[O:13])[CH:10]=[C:9]([C:14]([F:17])([F:16])[F:15])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][CH2:20]OC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>CCCCCC.C(Cl)Cl.C(OCC)(=O)C.C(Cl)(Cl)Cl>[CH3:18][O:19][CH2:20][N:12]1[C:11](=[O:13])[CH:10]=[C:9]([C:14]([F:16])([F:17])[F:15])[N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

9

Edukt 4

HCID 8020DimethoxymethaneHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)2×HCID 1354100074-Hydroxy-2-phenyl-6-(trifluoromethyl)pyrimidine

Produkt 1

HCID 196906963-methoxymethyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinoneAusbeute 32,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1.5 g (5.9 mmol) of 2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone, 17.2 g (226.3 mmol) dimethoxymethane, and 35 mL of chloroform was added 2.5 g (17.6 mmol) phosphorous pentoxide, at room temperature. By TLC (25% ethyl acetate in hexane) the reaction was incomplete after 4 h and an additional 3 g (21.1 mmol) phosphorous pentoxide was added. Stirring was continued for 16 h. The reaction mixture was poured onto crushed ice and 1M sodium hydroxide and methylene chloride were added. The layers were separated and the aqueous layer was extracted twice with methylene chloride. The organic extracts were combined and washed with brine, then dried over MgSO4 and concentrated to yield 1.1 g crude product, which was purified by recrystallization from hexane. Thus, 0.55 g (32%) 3-methoxymethyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (Compound 6) as a yellow solid was obtained. 1H-NMR (CDCl3) δ 3.55(3H,s); 5.2(2H,d); 6.85(1H,s); 7.65(3H,m); 7.75(2H,m).

Aufarbeitung

  1. customat room temperature
  2. additionThe reaction mixture was poured
  3. additionwere added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted twice with methylene chloride
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customto yield 1.1 g crude product, which
  10. customwas purified by recrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-8a76bfee244c4e589316dfef7559347f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726124

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