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

HRID 339742Notes

Reaction equation

HRID 339742 reaction equation
I[C:2]1[C:3](=O)[NH:4][CH:5]=[N:6][C:7]=1[CH3:8].[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.O=P(Cl)(Cl)[Cl:31]>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:31][C:3]1[C:2]([C:20]#[C:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([F:23])([F:22])[F:11])=[CH:14][CH:15]=2)=[C:7]([CH3:8])[N:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24813Phosphorus oxychlorideHCID 1354674485-Iodo-6-methylpyrimidin-4-olHCID 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

5-Iodo-6-methyl-4(3H)-pyrimidinone 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 compound. The compound was mixed with POCl3 and reacted while heating under reflux 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 compound
  3. customreacted
  4. temperaturewhile heating
  5. temperatureunder reflux
  6. customto obtain a target substance

Sources & evidence

ORD record
ord-752dad2ec84c49738826ff0222ea9410
Source dataset
uspto-grants-2014_11
Patent number
US08895565B2

Reaction notes

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