Sodium hydride → HCID 86704207, compound

HRID 624012Notes

Reaction equation

HRID 624012 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 86704207HCID 86704207, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-832a44f153694ebd9fc1c6d75eccc172
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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