Methanesulfonic Acid → HCID 178458291, compound

HRID 619158Notes

Reaction equation

HRID 619158 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O)[CH2:2][CH3:3].[C:13]([N:17]1[C:21]([NH2:22])=[C:20]([C:23]([NH2:25])=[O:24])[CH:19]=[N:18]1)([CH3:16])([CH3:15])[CH3:14].CS(O)(=O)=O>C(O)C>[C:13]([N:17]1[C:21]2=[N:22][C:7]([C:6]3[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=3[O:4][CH2:1][CH2:2][CH3:3])=[N:25][C:23](=[O:24])[C:20]2=[CH:19][NH:18]1)([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 2498072-Propoxy-benzaldehydeHCID 218460755-amino-1-tert-butyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178458291HCID 178458291, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-propoxybenzaldehyde (3.0 g, 18.27 mmol), 1-tert-butyl-5-amino-1H-pyrazole-4-carboxamide (2.5 g, 13.7 mmol), methanesulfonic acid (0.2 ml) and xylenes (50 ml) was refluxed overnight. The reaction mixture was stripped to dryness, treated with ethanol and again stripped to dryness. The residue was partitioned between chloroform and 10% KHCO3, the layers were separated, and the aqueous layer was extracted with chloroform (2×100 ml). The organic layers were combined, and concentrated in vacuo and the residue was dissolved in CH2Cl2 (30 ml) and combined with silica gel (20 g). The preloaded silica gel was placed on a silica gel column and eluted with 70% ether/hexanes, followed by ether (100%) to afford 0.98 g (22%) of 1-tert-butyl-6-(2-propoxyphenyl)pyrazolo[3,4-d]pyrimidin-4-one 1/100 hydrate, m.p. 130-131° C.

Workup

  1. temperaturewas refluxed overnight
  2. customThe residue was partitioned between chloroform and 10% KHCO3
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with chloroform (2×100 ml)
  5. concentrationconcentrated in vacuo
  6. dissolutionthe residue was dissolved in CH2Cl2 (30 ml)
  7. washeluted with 70% ether/hexanes

Sources & evidence

ORD record
ord-a7f8ce5aebe64f28861a8e3cc9caffae
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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