Potassium Carbonate → HCID 136333914, compound

HRID 1426419Notes

Reaction equation

HRID 1426419 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C[N:7](C)[C:8](=O)[CH3:9].[I-].[Na+].C[N:15](C)[C:16](=O)[CH3:17].Br[C:21]1[S:29][C:28]2[C:27](=[O:30])[NH:26][C:25]([CH2:31]Cl)=[N:24][C:23]=2[CH:22]=1.CN(C)C(=O)C.C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([N:3]([CH2:31][C:25]1[NH:26][C:27](=[O:30])[C:28]2[S:29][C:21]([C:9]3[CH:8]=[N:7][NH:15][C:16]=3[CH3:17])=[CH:22][C:23]=2[N:24]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 86676201HCID 86676201, compoundHCID 86676202HCID 86676202, compoundHCID 136333915HCID 136333915, compound

Product 1

HCID 136333914HCID 136333914, compound

Conditions

Temperature
70 °C

Procedure

0.57M Diethylamine/N,N-dimethylacetamide solution (0.7 mL), 0.15M sodium iodide/N,N-dimethylacetamide solution (0.2 mL), and 0.12 M 6-bromo-2-(chloromethyl)thieno[3,2-d]pyrimidin-4(3H)-one/N,N-dimethylacetamide solution (1.0 mL) were successively added to potassium carbonate (33.2 mg), and the mixture was stirred at 70° C. for 2.5 hr. Insoluble material was removed by filtration, and the filtrate was purified by high performance liquid chromatography {column: YMC CombiPrep Pro C18 RS (20 mm i.d.×50 mm L), mobile phase: acetonitrile/10% aqueous ammonium formate solution}. The obtained compound was dissolved in 1,2-dimethoxyethane (0.5 mL), 0.48M tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate/DME solution (0.5 mL), 0.96M aqueous calcium carbonate solution (0.5 mL), and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane complex (1:1) (10 mg) were added, and the mixture was stirred at 100° C. for 4 hr under a nitrogen atmosphere. Insoluble material was removed by filtration, and the filtrate was purified by high performance liquid chromatography {column: YMC CombiPrep Pro C18 RS (20 mm i.d.×50 mm L), mobile phase: acetonitrile/10% aqueous ammonium formate solution} to give the title compound (8.5 mg).

Workup

  1. customInsoluble material was removed by filtration
  2. customthe filtrate was purified by high performance liquid chromatography {column
  3. dissolutionThe obtained compound was dissolved in 1,2-dimethoxyethane (0.5 mL)
  4. addition0.48M tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate/DME solution (0.5 mL), 0.96M aqueous calcium carbonate solution (0.5 mL), and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane complex (1:1) (10 mg) were added
  5. stirringthe mixture was stirred at 100° C. for 4 hr under a nitrogen atmosphere
  6. customInsoluble material was removed by filtration
  7. customthe filtrate was purified by high performance liquid chromatography {column

Sources & evidence

ORD record
ord-646559648b874649851b8e73ee384764
Source dataset
uspto-grants-2015_01
Patent number
US08933069B2

Reaction notes

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