Trifluoroacetic acid → 4-Amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine

HRID 339740Notes

Reaction equation

HRID 339740 reaction equation
C(OC([NH:8][C:9]1[C:14](I)=[C:13]([CH3:16])[N:12]=[CH:11][N:10]=1)=O)(C)(C)C.[Br-].[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][Zn+])=[CH:22][CH:21]=1.O1CCCC1.FC(F)(F)C(O)=O>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>[NH2:8][C:9]1[C:14]([C:27]#[C:26][C:23]2[CH:24]=[CH:25][C:20]([C:19]([F:18])([F:29])[F:30])=[CH:21][CH:22]=2)=[C:13]([CH3:16])[N:12]=[CH:11][N:10]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 680024174-(tert-Butoxycarbonylamino)-5-iodo-6-methylpyrimidineHCID 178506165HCID 178506165, compound

Product 1

HCID 680024494-Amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

4-(tert-Butoxycarbonylamino)-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 compound. To the compound, trifluoroacetic acid was added to remove a tert-butoxycarbonyl group serving as a protecting group 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. customto remove a tert-butoxycarbonyl group
  4. customto obtain a target substance

Sources & evidence

ORD record
ord-748954c69c904686b94716429dc014aa
Source dataset
uspto-grants-2014_11
Patent number
US08895565B2

Reaction notes

Loading…