2,4-Dichloropyrimidine → 3-(2-Chloro-pyrimidin-4-yl)-benzaldehyde

HRID 2386583Notes

Reaction equation

HRID 2386583 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH:9]([C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1)=[O:10]>>[Cl:1][C:2]1[N:7]=[C:6]([C:15]2[CH:16]=[C:11]([CH:12]=[CH:13][CH:14]=2)[CH:9]=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 27343563-Formylphenylboronic acid

Product 1

HCID 249019653-(2-Chloro-pyrimidin-4-yl)-benzaldehydeYield 60%

Procedure

2,4 dichloropyrimidine and 3-formyl phenyl boronic acid were coupled following procedure A. The yield was 60%. LC-MS showed the product was >95% pure and had the expected M+H+ of 219. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) 10.1 (s, 1H) 8.7 (d, 1H) 8.6 (m, 1H) 8.4 (m, 1H) 8.1 (m, 1H) 7.7 (m, 2H).

Sources & evidence

ORD record
ord-19469dba563d4010a68a2c5ab369e52e
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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