Sodium Acetate → Ethyl 6-[(acetyloxy)methyl]-2-(trifluoromethyl)pyrimidine-4-carboxylate

HRID 1617415노트

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HRID 1617415 반응식
Br[CH2:2][C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1.[C:18]([O-:21])(=[O:20])[CH3:19].[Na+]>C(#N)C>[C:18]([O:21][CH2:2][C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1)(=[O:20])[CH3:19]

참가 물질

4

반응물 2

HCID 517045Sodium AcetateHCID 58431340Ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate

생성물 1

HCID 58431332Ethyl 6-[(acetyloxy)methyl]-2-(trifluoromethyl)pyrimidine-4-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

Ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate (1.62 g, 5.17 mmol, from Step A) was dissolved in acetonitrile (15 mL) and sodium acetate (2.8 g, 34 mmol) was added. The mixture was heated to 80° C. for 4 hours, then stood at room temperature overnight. Acetonitrile was removed in vacuo. The residue was partitioned between water and ethyl acetate and the aqueous layer was extracted with two further portions of ethyl acetate. The combined extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with a gradient from 0-60% ethyl acetate/hexane afforded purified product. Yield: 0.95 g (63%); LC-MS: 293.0 (M+H)+. 1H NMR (300 MHz, CDCl3): δ 8.15 (s, 1H), 5.36 (s, 2H), 4.53 (q, 2H), 2.25 (s, 3H), 1.46 (t, 3H).

후처리

  1. customAcetonitrile was removed in vacuo
  2. customThe residue was partitioned between water and ethyl acetate
  3. extractionthe aqueous layer was extracted with two further portions of ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washFlash chromatography, eluting with a gradient from 0-60% ethyl acetate/hexane
  9. customafforded
  10. custompurified product

출처 및 근거

ORD 기록
ord-0410eff0267045f0abd12e7e87b90cb4
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765734B2

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