Hydrochloric Acid → 3-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

HRID 2364073Notes

Reaction equation

HRID 2364073 reaction equation
CC1(C)[NH:7][C:6]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][NH:14][C:15]=3[CH3:16])[S:10][C:5]=2[C:4](=[O:17])[NH:3]1.Cl>CO>[NH2:7][C:6]1[CH:8]=[C:9]([C:11]2[CH:12]=[N:13][NH:14][C:15]=2[CH3:16])[S:10][C:5]=1[C:4]([NH2:3])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66743505Cdc7-IN-15

Product 1

HCID 667430133-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamideYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,2-dimethyl-6-(5-methyl-1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (1.97 g, 7.51 mmol), 1 M aqueous HCl. (38 mL) and MeOH (38 mL) was stirred at 50° C. for 4 h. After removal of the solvent at reduced pressure, the organic materials were extracted with EtOAc/THF. The combined extracts were dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, EtOAc to 90:10 EtOAc/MeOH) to give the title compound (1.20 g, 72%) as a green solid:

Workup

  1. customAfter removal of the solvent at reduced pressure
  2. extractionthe organic materials were extracted with EtOAc/THF
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customAfter removal of the solvent at reduced pressure
  6. customthe residue was purified by column chromatography (Purif, silica gel, EtOAc to 90:10 EtOAc/MeOH)

Sources & evidence

ORD record
ord-d365f5cec34a4d97ab8567ace77df18c
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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