Potassium Phosphate, Tribasic → HCID 68074163, compound

HRID 2364015Notes

Reaction equation

HRID 2364015 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]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[N:30][N:31](C(OC(C)(C)C)=O)[CH:32]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C>[CH3:12][C:6]1([CH3:13])[N:5]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:4]2[CH:3]=[C:2]([C:28]3[CH:29]=[N:30][NH:31][CH:32]=3)[S:10][C:9]=2[C:8](=[O:11])[NH:7]1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 86662296HCID 86662296, compound

Product 1

HCID 68074163HCID 68074163, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with ethyl (6-bromo-2,2-dimethyl-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-1(2H)-yl)acetate (120 mg, 0.346 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (288 mg, 0.978 mmol), K3PO4 (277 mg, 1.3 mmol) and DMF (1 mL). The flask was purged with argon. Then, 1,1′-bis(diphenylphosphino) ferrocenepalladium (II) dichloride dichloromethane adduct (8.0 mg, 0.0098 mmol) was added to the mixture. The flask was purged with argon again. After stirring at 50° C. for 18 h and at 80° C. for 18 h, water and EtOAc were added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, 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), then crystallized from MeOH/EtOAc/heptane to give the title compound (5.6 mg, 5%) as a brown solid:

Workup

  1. customThe flask was purged with argon
  2. customThe flask was purged with argon again
  3. additionwater and EtOAc were added
  4. customto quench
  5. customthe reaction
  6. extractionThe organic materials were extracted with EtOAc
  7. washThe combined extracts were washed with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customAfter removal of the solvent at reduced pressure
  11. customthe residue was purified by column chromatography (Purif, silica gel, EtOAc to 90:10 EtOAc/MeOH)
  12. customcrystallized from MeOH/EtOAc/heptane

Sources & evidence

ORD record
ord-74baa148ec8742c0b8bed0f9c1c73e33
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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