Water → HCID 59732358, compound

HRID 131200Notes

Reaction equation

HRID 131200 reaction equation
C1C=CC([As](C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[C:21]1[C:25]2[N:26]=[C:27]([N:35]([CH3:37])[CH3:36])[N:28]=[C:29]([C:30]3[O:31][CH:32]=[CH:33][CH:34]=3)[C:24]=2[S:23][CH:22]=1.C([Sn](CCCC)(CCCC)[C:43]1[O:44][CH:45]=[CH:46][CH:47]=1)CCC.O>CN(C=O)C>[O:31]1[CH:32]=[CH:33][CH:34]=[C:30]1[C:29]1[C:24]2[S:23][CH:22]=[C:21]([C:43]3[O:44][CH:45]=[CH:46][CH:47]=3)[C:25]=2[N:26]=[C:27]([N:35]([CH3:37])[CH3:36])[N:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11773TriphenylarsineHCID 43936882-(Tributylstannyl)furanHCID 59732374HCID 59732374, compound

Product 1

HCID 59732358HCID 59732358, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of AsPh3 (73 mg, 0.24 mmol) in DMF (2 mL) was treated with Pd(OAc)4 (13 mg, 0.06 mmol), stirred at room temperature for 10 min, treated with 7-bromo-N,N-dimethyl-4-(2-furyl)thieno[3,2-d]pyrimidine-2-amine (194 mg, 0.6 mmol) and 2-(tributylstannyl)-furan (340 μL, 1.1 mmol), heated to 100° C. for 16 h, cooled, poured into water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purified by chromatography (SiO2:EtOAc:Heptane, 1:9) to give the title compound (27 mg, 15%) as a orange solid.

Workup

  1. temperatureheated to 100° C. for 16 h
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography (SiO2:EtOAc:Heptane, 1:9)

Sources & evidence

ORD record
ord-136ef46697bd4d89ba4b40768b9bbbd7
Source dataset
uspto-grants-2008_06
Patent number
US07384949B2

Reaction notes

Loading…