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

HRID 14983

Reaction equation

HRID 14983 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-865e1b4d39e34a55adfe40d5054d0d71
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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