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

HRID 1455

反应方程式

HRID 1455 反应方程式
[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

参与物

9

反应物 4

HCID 8020甲缩醛HCID 14798二甲基对苯二胺二盐酸HCID 14812Phosphorus oxide (P4O10)2 次HCID 1354100072-苯基-4-羟基-6-三氟甲基嘧啶

产物 1

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

试剂、催化剂与溶剂 4

HCID 6212三氯甲烷溶剂HCID 6344二氯甲烷溶剂HCID 8058正己烷溶剂HCID 8857乙酸乙酯溶剂

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-8a76bfee244c4e589316dfef7559347f
来源数据集
uspto-grants-1998_03
专利号
US05726124

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