Sodium Methoxide → tert-Butyl 4-(5-methoxy-pyrazolo[1,5-a]pyrimidin-7-yl)piperazine-1-carboxylate

HRID 333969Notes

Reaction equation

HRID 333969 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[N:5]2[N:21]=[CH:22][CH:23]=[C:4]2[N:3]=1.[CH3:24][O-:25].[Na+]>CO>[CH3:24][O:25][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[N:5]2[N:21]=[CH:22][CH:23]=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86691599tert-Butyl 4-(5-chloro-pyrazolo[1,5-a]pyrimidin-7-yl)piperazine-1-carboxylate

Product 1

HCID 86691598tert-Butyl 4-(5-methoxy-pyrazolo[1,5-a]pyrimidin-7-yl)piperazine-1-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

tert-Butyl 4-(5-chloro-pyrazolo[1,5-a]pyrimidin-7-yl)piperazine-1-carboxylate (1.23 g, 3.65 mmol) was dissolved under an argon atmosphere in anhydrous methanol (6 ml). Sodium methanolat (3.65 ml of a 1M solution in methanol) was added and the mixture was heated under reflux for 9 hours. The solvent was removed under reduced pressure, the residue taken up in dichloromethane, the resulting solution was washed with water, dried over magnesium sulfate, the solvent removed under reduced pressure to yield 1.186 g of a solid (3.56 mmol, 98%). MS (APCI): m/z=334.3 [M+1]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 9 hours
  3. customThe solvent was removed under reduced pressure
  4. washthe resulting solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b88dc047dbe140f4920fcce943de36a9
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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