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

HRID 1455

反応式

HRID 1455 の反応式
[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

参加物

9

反応物 4

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

生成物 1

HCID 196906963-methoxymethyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone収率 32.8%

試薬・触媒・溶媒 4

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8a76bfee244c4e589316dfef7559347f
出典データセット
uspto-grants-1998_03
特許番号
US05726124

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