1,1,3,3-Tetraethoxy-2-methylpropane → 6-Methyl-2-phenylpyrazolo[1,5-a]pyrimidine

HRID 1926790Notes

Reaction equation

HRID 1926790 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([NH2:12])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH:16](OCC)[CH:17]([CH3:25])[CH:18](OCC)OCC)C>CC(O)=O>[CH3:25][C:17]1[CH:16]=[N:12][C:10]2[N:9]([N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 827611,1,3,3-Tetraethoxy-2-methylpropaneHCID 1366553-Amino-5-phenylpyrazole

Product 1

HCID 577430576-Methyl-2-phenylpyrazolo[1,5-a]pyrimidineYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-phenyl-1H-pyrazol-5-amine x120 (31.4 mmol, 1 eq, 5 g) in AcOH (30 ml) is added 1,1,3,3-tetraethoxy-2-methylpropane x121 (31.4 mmol, 1 eq, 7.36 g). The mixture is heated at 100° C. during 4 hours. After evaporation of the solvent under reduced pressure, the crude product is poured in saturated NaHCO3 aqueous solution and then extracted with AcOEt. The cumulated organic layers are dried over MgSO4, filtered and evaporated under reduce pressure. The crude mixture is recristallized in AcOEt to afford 6-methyl-2-phenylpyrazolo[1,5-a]pyrimidine x122 as a solid (3 g).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. additionthe crude product is poured in saturated NaHCO3 aqueous solution
  3. extractionextracted with AcOEt
  4. dry with materialThe cumulated organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-425163fa8ae44b049a7ed736bdf344bb
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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