Trimethylsilylacetylene → 4-Chloro-6-trimethylsilanylethynyl-thieno[3,2-d]pyrimidine

HRID 1818942Notes

Reaction equation

HRID 1818942 reaction equation
Br[C:2]1[S:10][C:9]2[C:8]([Cl:11])=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14]>C1COCC1.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.[Cu]I>[Cl:11][C:8]1[C:9]2[S:10][C:2]([C:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12])=[CH:3][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 183827966-Bromo-4-chlorothieno(3,2-d)pyrimidine

Product 1

HCID 858432224-Chloro-6-trimethylsilanylethynyl-thieno[3,2-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  1. customwas flushed with dry N2 for several minutes
  2. customThe solvent was removed
  3. customthe residue purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-c01a34cc09b04001996507755cc0c5fa
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

Loading…