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Triethylamine → 1-(4-Trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)-1-trimethylacetoxymethane

HRID 861392
Notes
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Reaction equation

HRID 861392 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[F:8][C:9]([F:27])([F:26])[C:10]1[C:15]([CH:16]([C:18]2[C:19]([O:24][CH3:25])=[N:20][CH:21]=[N:22][CH:23]=2)[OH:17])=[CH:14][N:13]=[CH:12][N:11]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>[F:27][C:9]([F:8])([F:26])[C:10]1[C:15]([CH:16]([C:18]2[C:19]([O:24][CH3:25])=[N:20][CH:21]=[N:22][CH:23]=2)[O:17][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[CH:14][N:13]=[CH:12][N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 62493Pivaloyl chlorideHCID 197028001-(4-Trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)methanol

Product 1

HCID 676303761-(4-Trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)-1-trimethylacetoxymethaneYield 80.1%

Reagents, catalysts & solvents

2
HCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Trimethylacetyl chloride (36 μl, 35.1 mg, 0.28 mmol, 3.2 equivalent) was added via syringe to a solution of 1-(4-trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)methanol (25.1 mg, 0.0877 mmol), triethylamine (70 μl, 50.5 mg, 0.50 mmol, 5.7 equivalents) and dimethylaminopyridine (DMAP) (cat.) in toluene (5 ml) and the solution heated to reflux for 2 hours. The solution was cooled, diluted with NaHCO3 (sat.), and extracted with EtOAc (3 times). The combined extracts were washed with brine (sat.), dried (MgSO4), filtered and concentrated in vacuo. Preparative thin layer chromatography (SiO2 ; hexane/EtOAc, 1:1) gave 26 mg of 1-(4-trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)-1-trimethylacetoxymethane as a solid.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe solution was cooled
  4. extractionextracted with EtOAc (3 times)
  5. washThe combined extracts were washed with brine (sat.)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-975db8ccb89b43608e1fa2bb8d2afb8f
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05714438

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes