HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1818942Generated: October 27, 2026
Trimethylsilylacetylene → 4-Chloro-6-trimethylsilanylethynyl-thieno[3,2-d]pyrimidine
https://huagongshe.com/reaction/1818942
Participants
| Role | Name | HCID | Charge |
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| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 6-Bromo-4-chlorothieno(3,2-d)pyrimidine | HCID 18382796 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(benzonitrile)palladium chloride | HCID 498840 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Chloro-6-trimethylsilanylethynyl-thieno[3,2-d]pyrimidine | HCID 85843222 | — |
Reaction Steps
A mixture of 6-bromo-4-chloro-thieno[3,2-d]pyrimidine (10.0 mmol), (trimethylsilyl)acetylene (12.0 mmol), Pd(PhCN)2Cl2, (1.0 mmol), CuI (1.0 mmol) and TEA (2.0 mmol) in dry THF (60.0 mL) was flushed with dry N2 for several minutes and stirred at 60° C. for 30 minutes under an atmosphere of N2. The solvent was removed and the residue purified by flash column chromatography on silica gel to provide 4-chloro-6-trimethylsilanylethynyl-thieno[3,2-d]pyrimidine (compound 48.1) in 65% yield. EIMS (m/z): calcd. for C11H11ClN2SSi (M+)+H 266.01. found 266.00.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07601725B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-c01a34cc09b04001996507755cc0c5fa |
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| Source note | uspto-grants-2009_10 |
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