Bromine → 7-bromo-2,2-dimethyl-6-(5-methyl-1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2364036Notes

Reaction equation

HRID 2364036 reaction equation
[CH3:1][C:2]1([CH3:18])[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.[Br:19]Br.C([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:19][C:8]1[C:6]2[NH:7][C:2]([CH3:18])([CH3:1])[NH:3][C:4](=[O:17])[C:5]=2[S:10][C:9]=1[C:11]1[CH:12]=[N:13][NH:14][C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 66743505Cdc7-IN-15

Product 1

HCID 667438547-bromo-2,2-dimethyl-6-(5-methyl-1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a vigorously stirred solution of 2,2-dimethyl-6-(5-methyl-1H-pyrazol-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.080 g, 0.305 mmol) in acetic acid (2 mL) was added slowly bromine (0.019 mL, 0.366 mmol). After 5 min, the mixture was poured into excess saturated aqueous NaHCO3 and extracted with EtOAc, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was mixed with acetone (5 mL), PTSA (3 mg) and DMF (1 mL). The mixture was stirred for 30 min at 70° C. and poured into saturated aqueous NaHCO3 and extracted with EtOAc, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc) to give a yellow solid. This solid was triturated with EtOAc/hexane, and the precipitate was collected by filtration to afford the title compound (65.4 mg, 63%) as a yellow solid:

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe extract was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was mixed with acetone (5 mL), PTSA (3 mg) and DMF (1 mL)
  6. additionpoured into saturated aqueous NaHCO3
  7. extractionextracted with EtOAc
  8. dry with materialthe extract was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc)
  12. customto give a yellow solid
  13. customThis solid was triturated with EtOAc/hexane
  14. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2358e9f73cef41faa6192d3716a9a417
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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