5-Phenyl-1-pentyne → 4-Methyl-6-(5-phenyl-pent-1-ynyl)-pyrimidine

HRID 1967212Notes

Reaction equation

HRID 1967212 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4](OS(C2C=CC(C)=CC=2)(=O)=O)[CH:3]=1.[CH2:19]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:20][CH2:21][C:22]#[CH:23]>CCCCCCC.CCOC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([C:23]#[C:22][CH2:21][CH2:20][CH2:19][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 745735-Phenyl-1-pentyneHCID 86646621Toluene-4-sulfonic acid 6-methyl-pyrimidin-4-yl ester

Product 1

HCID 252221794-Methyl-6-(5-phenyl-pent-1-ynyl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 6-methyl-pyrimidin-4-yl ester and pent-4-ynyl-benzene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 8:2; yield (36.6 mg, 31%); 1H NMR δ (CDCl3): 9.01 (s, 1H), 7.31-7.25 (m, 2H), 7.22-7.16 (m, 4H), 2.78 (t, J=7.18 Hz, 2H), 2.51 (s, 3H), 2.41 (t, J=7.17 Hz, 2H), 1.93 (p, J=7.22 Hz, 2H); LCMS m/z: 236.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (36.6 mg, 31%)

Sources & evidence

ORD record
ord-5536ca06c8444846ba70254ff57e109f
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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