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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 32606Generated: October 29, 2026

5-Tributylstannyl-4-iodo-1-methyl-1H-imidazole → 6-(4-Iodo-1-methyl-1H-imidazol-5-yl)-4-methylthio-thieno[2,3-d]pyrimidine

https://huagongshe.com/reaction/32606

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-Tributylstannyl-4-iodo-1-methyl-1H-imidazoleHCID 17965785—
Reactant4-Methylthio-6-iodo-thieno[2,3-d]pyrimidineHCID 17965821—
CatalystHCID 178418397HCID 178418397—
SolventDimethylformamideHCID 6228—
Product6-(4-Iodo-1-methyl-1H-imidazol-5-yl)-4-methylthio-thieno[2,3-d]pyrimidineHCID 6919680267.3%

Reaction Conditions

Temperature100 °C

Reaction Steps

4-Methylthio-6-iodo-thieno[2,3-d]pyrimidine (Intermediate 91) (949 mg), 5-tributylstannyl-4-iodo-1-methyl-1H-imidazole (Intermediate 92) (2.76 g) and tetrakis(triphenylphosphine)palladium(0) (178 mg) were stirred in anhydrous DMF (50 mL), degassed with nitrogen for 10 min, then heated to 100° C. for 18 hours under an inert atmosphere. The reaction mixture was concentrated in vacuo and the crude product triturated with DCM (20 mL) to afford the title compound as a yellow solid (805 mg, 67%);

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07427616B2
Source datasetuspto-grants-2008_09
ORD IDord-30357bc705ba40d99b2de1f23d4a355d
Source noteuspto-grants-2008_09