乙醇 → 4-Ethoxy-2-methylthio-6-[3-(trifluoromethyl)phenoxy]pyrimidine

HRID 801

反应方程式

HRID 801 反应方程式
[CH2:1]([OH:3])[CH3:2].[H-].[Na+].Cl[C:7]1[CH:12]=[C:11](Cl)[N:10]=[C:9]([S:14][CH3:15])[N:8]=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1>C1COCC1.CN(C=O)C>[CH2:1]([O:3][C:7]1[CH:12]=[C:11]([O:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:25])[F:26])[CH:19]=2)[N:10]=[C:9]([S:14][CH3:15])[N:8]=1)[CH3:2]

参与物

7

反应物 4

HCID 702乙醇HCID 7376间三氟甲基苯酚HCID 24758氢化钠2 次HCID 805314,6-二氯-2-甲基硫烷基嘧啶

产物 1

HCID 196938684-Ethoxy-2-methylthio-6-[3-(trifluoromethyl)phenoxy]pyrimidine

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺溶剂HCID 8028四氢呋喃溶剂

实验过程

Ethanol (1.18 g, 0.0256×1.0 mol) and NaH (1.02 g, (ca.60% in mineral oil), 0.0256×1.0 mol) were dissolved in THF and 4,6-dichloro-2-methylthiopyrimidine (Compound No. VII-23)(5.0 g, 0.0256 mol) was added thereto. The resulting solution was stirred for about 30 minutes at room temperature. To this reaction solution, m-trifluoromethyl-phenol (6.23 g, 0.0256×1.5 mol), NaH (1.54 g, (ca.60% in mineral oil), 0.0256×1.5 mol), and KI (2.12 g, 0.0256×0.5 mol) dissolved in DMF were added. The resulting solution was refluxed for about 7 hours. The reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate to separate an organic phase. The organic phase was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, and thereafter purified on a silica gel column.

后处理

  1. additionVII-23)(5.0 g, 0.0256 mol) was added
  2. additionwere added
  3. temperatureThe resulting solution was refluxed for about 7 hours
  4. customThe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
  5. customto separate an organic phase
  6. washThe organic phase was washed with aqueous saturated sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified on a silica gel column

来源与证据

ORD记录
ord-0c41a886f892437a80e1ebfc69bc8999
来源数据集
uspto-grants-1998_03
专利号
US05723412

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