Triphenylarsine → HCID 86603177, compound

HRID 1818948Notes

Reaction equation

HRID 1818948 reaction equation
[Cl:1][C:2]1[C:3]2[S:10][C:9]([Sn](CCCC)(CCCC)CCCC)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.I[C:25]1[CH:26]=[N:27][N:28]([CH2:30][CH2:31][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:29]=1.[As](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:25]3[CH:26]=[N:27][N:28]([CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)[CH:29]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 3

HCID 11773TriphenylarsineHCID 567769944-Chloro-6-(tributylstannyl)thieno[3,2-d]pyrimidineHCID 64429562HCID 64429562, compound

Product 1

HCID 86603177HCID 86603177, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Compound 52.1 (22.58 mmol) and 4-iodo-1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazole (22.32 mmol) was dissolved in DMF and degassed with nitrogen. To this was added Pd2(dba)3 (0.23 mmol), Ph3As (0.46 mmol) and CuI (1.16 mmol). The reaction mixture was heated at 80° C. for 6 hours, concentrated to dryness and purified by flash column chromatography on silica gel (10% MeOH in dichloromethane) to provide 4-chloro-6-[1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-thieno[3,2-d]pyrimidine (compound 52.2).

Workup

  1. customdegassed with nitrogen
  2. concentrationconcentrated to dryness
  3. custompurified by flash column chromatography on silica gel (10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-cf77406481f64b99a5b9dd6734cad972
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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