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

HRID 2364063Notes

Reaction equation

HRID 2364063 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][NH:14][C:15]=3[CH3:16])[S:10][C:6]=2[C:5](=[O:17])[NH:4]C1(C)C.Cl.C([O-])(O)=O.[Na+]>CO>[CH3:1][NH:2][C:7]1[CH:8]=[C:9]([C:11]2[CH:12]=[N:13][NH:14][C:15]=2[CH3:16])[S:10][C:6]=1[C:5]([NH2:4])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 667433211,2,2-trimethyl-6-(5-methyl-1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

Product 1

HCID 667434763-(methylamino)-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamideYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1,2,2-trimethyl-6-(5-methyl-1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (378 mg, 1.37 mmol), 1 M HCl (4.79 mL) and MeOH (12 mL) was stirred for 2 h at 50° C. The mixture was poured into excess saturated aqueous NaHCO3 and extracted with 3:1 EtOAc/THF, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was triturated with ethanol (6 mL) and collected by filtration to afford the title compound (183 mg, 57%) as a pale yellow solid:

Workup

  1. extractionextracted with 3:1 EtOAc/THF
  2. dry with materialthe extract was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with ethanol (6 mL)
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3f064ab5e7aa4f20a81c864c722ba6b7
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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