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

HRID 861392
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HRID 861392 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-975db8ccb89b43608e1fa2bb8d2afb8f
출처 데이터셋
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05714438

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