1,2-Dimethoxyethane → 5-ethyl-N,N-dimethyl-4-(1,2,2-trimethyl-4-oxo-1,2,3,4-tetrahydrothieno[3,2-d]pyrimidin-6-yl)-1H-pyrazole-1-sulfonamide

HRID 2364046Notes

Reaction equation

HRID 2364046 reaction equation
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[N:5]([CH3:14])[C:4]=2[CH:3]=1.[CH2:15]([C:17]1[N:21]([S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[N:20]=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1)[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>O>[CH2:15]([C:17]1[N:21]([S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[N:20]=[CH:19][C:18]=1[C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[N:5]([CH3:14])[C:4]=2[CH:3]=1)[CH3:16]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 667439846-bromo-1,2,2-trimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneHCID 667440175-ethyl-N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-sulfonamide

Product 1

HCID 667436105-ethyl-N,N-dimethyl-4-(1,2,2-trimethyl-4-oxo-1,2,3,4-tetrahydrothieno[3,2-d]pyrimidin-6-yl)-1H-pyrazole-1-sulfonamideYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromo-1,2,2-trimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (138 mg, 0.50 mmol), 5-ethyl-N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-sulfonamide (329 mg, 1.00 mmol), cesium carbonate (815 mg, 2.50 mmol), 1,2-dimethoxyethane (5 mL) and water (1.25 mL) was purged with argon. Then, 1,1′-bis(diphenylphosphino) ferrocenepalladium (II) dichloride dichloromethane adduct (40.8 mg, 0.050 mmol) was added, and the mixture was purged with argon again. The mixture was stirred at 90° C. for 1 h. The mixture was poured into water (100 mL) and EtOAc (200 mL). The insoluble materials were filtered off, and the organic layer was collected from the filtrate. This organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residual oil was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc) to afford the title compound (139 mg, 70%) as a yellow solid:

Workup

  1. customwas purged with argon
  2. customthe mixture was purged with argon again
  3. additionThe mixture was poured into water (100 mL) and EtOAc (200 mL)
  4. filtrationThe insoluble materials were filtered off
  5. customthe organic layer was collected from the filtrate
  6. washThis organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residual oil was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc)

Sources & evidence

ORD record
ord-a87473ea81a84c5e8daa648cfe4a8e0f
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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