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

HRID 2386299Notes

Reaction equation

HRID 2386299 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) δ10.1 (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-bf37b612af4a4be49e59557db5eacbba
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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