Tetrahydrofuran → 4-Chloro-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine

HRID 339741Notes

Reaction equation

HRID 339741 reaction equation
[Cl:1][C:2]1[C:7](I)=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=1.[Br-].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][Zn+])=[CH:15][CH:14]=1.O1CCCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[Cl:1][C:2]1[C:7]([C:20]#[C:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([F:11])([F:22])[F:23])=[CH:14][CH:15]=2)=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 127953694-Chloro-5-iodo-6-methylpyrimidineHCID 178506165HCID 178506165, compound

Product 1

HCID 866607054-Chloro-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

4-Chloro-5-iodo-6-methylpyrimidine and [4-(trifluoromethyl)phenyl]ethynylzinc bromide were reacted in a solvent mixture of tetrahydrofuran and N,N-dimethylformamide (1:1) in the presence of tetrakis(triphenylphosphine)palladium while stirring under room temperature to heating to obtain a target substance. The target substance was subjected to e.g., proton nuclear magnetic resonance spectrometry (1H-NMR) and mass spectrometry (MS) and confirmed as the titled compound. Furthermore, MS measurement result is shown.

Workup

  1. temperatureto heating
  2. customto obtain a target substance

Sources & evidence

ORD record
ord-7ff425dc09554ccb9bbb4bc7be5e1542
Source dataset
uspto-grants-2014_11
Patent number
US08895565B2

Reaction notes

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