2,4-Dichloropyrimidine → 2-Chloro-4-[2-(4-fluorophenyl)ethynyl]pyrimidine

HRID 885638Notes

Reaction equation

HRID 885638 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)#[CH:10]>>[Cl:1][C:2]1[N:7]=[C:6]([C:10]#[C:9][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 5226271-Ethynyl-4-fluorobenzene

Product 1

HCID 121652312-Chloro-4-[2-(4-fluorophenyl)ethynyl]pyrimidine

Procedure

The title compound was prepared from 2,4-dichloropyrimidine and 1-ethynyl-4-fluorobenzene using methods analogous to those described in Example 2 (65%). TLC (25% EtOAc/hexanes): Rf=0.21. mp 125-126° C. IR: 3049 (w), 2210 (w), 1559 (s). 1H NMR (CDCl3): 8.61 (d, J=5.0 Hz, 1H), 7.70-7.60 (m, 2H), 7.38 (d, J=5.0 Hz, 1H), 7.13-7.06 (m, 2H). 13C NMR (CDCl3): 163.99 (d, JC-F=252 Hz), 161.86, 159.66, 153.39, 134.96 (d, JC-F=8.6 Hz), 121.77, 116.96 (d, JC-F=3.4 Hz), 116.40 (d, JC-F=22 Hz), 95.27, 85.89. Anal. Calcd for C12H6ClFN2: C, 61.95; H, 2.60; N, 12.04. Found: C, 62.15; H, 2.83; N, 12.00.

Sources & evidence

ORD record
ord-6e23aa285cd24385a1a5d63865966a40
Source dataset
uspto-grants-2012_08
Patent number
US08242273B2

Reaction notes

Loading…