Sodium hydride → HCID 86704207, 화합물

HRID 624012노트

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HRID 624012 반응식
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][OH:11])[CH:8]=1)([O-:3])=[O:2].[H-].[Na+].Cl[C:15]1[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[N:16]=1>C1COCC1>[CH3:24][O:23][C:17]1[CH:18]=[C:19]([O:21][CH3:22])[N:20]=[C:15]([O:11][CH2:10][CH2:9][N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[N:6]2)[N:16]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 1620552-(4-Nitro-1H-pyrazol-1-yl)ethan-1-olHCID 51523232-Chloro-4,6-dimethoxypyrimidine

생성물 1

HCID 86704207HCID 86704207, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To an ice-cooled solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanol (1.90 g, 12.02 mmol) in THF (60 mL), NaH (673 mg, 16.82 mmol, 60%) was added and the solution was stirred for 5 min at 0° C., then the ice bath was removed and the reaction mixture was stirred at rt for 30 min, before 2-chloro-4,6-dimethoxypyrimidine (2.31 g, 13.22 mmol) was added. After 40 min at rt, the reaction mixture was quenched with water and the org. solvent was removed in vacuo. The aq. layer was extracted with DCM (1×), then acidified with 1 N HCl-solution to pH 2, and extracted with DCM (2×). The combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent removed under reduced pressure. Purification by crystallization (DCM-hept-mixture) yielded 4,6-dimethoxy-2-(2-(4-nitro-1H-pyrazol-1-yl)ethoxy)pyrimidine as a beige solid. LC-MS conditions A: tR=0.88 min, [M+H]+=295.98.

후처리

  1. additionwas added
  2. customthe ice bath was removed
  3. additionwas added
  4. waitAfter 40 min at rt
  5. customthe reaction mixture was quenched with water
  6. customsolvent was removed in vacuo
  7. extractionThe aq. layer was extracted with DCM (1×)
  8. extractionextracted with DCM (2×)
  9. washlayers were washed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure
  13. customPurification
  14. customby crystallization (DCM-hept-mixture)

출처 및 근거

ORD 기록
ord-832a44f153694ebd9fc1c6d75eccc172
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303023B2

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