2-(Tributylstannyl)furan → HCID 178508305, compound

HRID 750496Notes

Reaction equation

HRID 750496 reaction equation
Cl[C:2]1[C:3]2[NH:11][N:10]=[N:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.C([Sn](CCCC)(CCCC)[C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)CCC>CN1CCCC1=O.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:2]1[C:3]2[NH:11][N:10]=[N:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

6

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 178508438HCID 178508438, compound

Product 1

HCID 178508305HCID 178508305, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 7-chloro-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (570 mg, 3.34 mmol) in N-methyl-2-pyrrolidinone (4 mL) was treated with PdCl2(PPh3)2 (117 mg, 0.17 mmol) and 2-(tributylstannyl)furan (1.05 mL, 1 mmol), stirred at 80° C. for 5 h, diluted with EtOAc, filtered through a silica pad and concentrated in vacuo. The residue was triturated with diethyl ether and the title compound isolated as a yellow solid (438 mg, 65%).

Workup

  1. filtrationfiltered through a silica pad
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-d3302b3fc7c647269d343aff2399bb51
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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