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

HRID 2364047Notes

Reaction equation

HRID 2364047 reaction equation
[Br:1][C:2]1[C:6]2[NH:7]C(C)(C)[NH:9][C:10](=[O:11])[C:5]=2[S:4][C:3]=1[C:14]1[CH:15]=[N:16][NH:17][CH:18]=1.Cl.C([O-])(O)=O.[Na+]>CO>[NH2:7][C:6]1[C:2]([Br:1])=[C:3]([C:14]2[CH:15]=[N:16][NH:17][CH:18]=2)[S:4][C:5]=1[C:10]([NH2:9])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 667432407-bromo-2,2-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

Product 1

HCID 667431873-amino-4-bromo-5-(1H-pyrazol-4-yl)thiophene-2-carboxamideYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-bromo-2,2-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (243 mg, 0.743 mmol), 1 M HCl (2.60 mL, 2.60 mmol) and MeOH (7 mL) was stirred at 50° C. for 2 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with 3:1 EtOAc/THF, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound (147 mg, 69%) 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

Sources & evidence

ORD record
ord-acf88a9593a54391a1b6b5832f900ec8
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

Loading…