HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 801
Notes
Print preview

Reaction equation

HRID 801 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydride2×HCID 805314,6-Dichloro-2-(methylthio)pyrimidine

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0c41a886f892437a80e1ebfc69bc8999
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723412

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes