3-Butyn-1-OL → HCID 68425529, compound

HRID 1818927Notes

Reaction equation

HRID 1818927 reaction equation
Br[C:2]1[S:10][C:9]2[C:8]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:32])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)=[CH:16][CH:15]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH2:33]([OH:37])[CH2:34][C:35]#[CH:36]>N1CCCCC1.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.[Cu]I>[OH:37][CH2:33][CH2:34][C:35]#[C:36][C:2]1[S:10][C:9]2[C:8]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:32])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)=[CH:16][CH:15]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 135663-Butyn-1-OLHCID 68423734HCID 68423734, compound

Product 1

HCID 68425529HCID 68425529, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 8082PiperidineSolvent

Procedure

To a nitrogen purged solution of compound 20.2 (0.79 mmol), 3-butyn-1-ol (2.5 equivalents), Pd(PhCN)2Cl2 (0.2 equivalent) in piperidine was added CuI (0.5 equivalent) followed by stirring at room temperature for 3 hours. The reaction mixture was then subjected to an aqueous work-up and purified by flash column chromatography on silica gel to provide N-(4-{2-[6-(4-hydroxy-but-1-ynyl)-thieno[3,2-d]pyrimidin-4-ylamino]-ethyl}-phenyl)-3-trifluoromethyl-benzamide (compound 23.1).

Workup

  1. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-445448a21ec84f84b20fb22bb2e76c66
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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