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

HRID 1455

반응식

HRID 1455 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 6212Chloroform용매HCID 6344Dichloromethane용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8a76bfee244c4e589316dfef7559347f
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726124

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