2,4-Dichloropyrimidine → HCID 86603334, compound

HRID 14978Notes

Reaction equation

HRID 14978 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13]>>[Cl:1][C:2]1[N:7]=[C:6]([C:17]2[C:10]([CH3:9])=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 707011482-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Product 1

HCID 86603334HCID 86603334, compoundYield 50%

Procedure

2,4 dichloropyrimidine and 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde was coupled following procedure A. The yield was 50%. LC-MS showed the product was >95% pure and had the expected M+H+ of 233. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 9.9 (s, 1H) 8.6 (s, 1H) 7.5 (d, 2H) 7.4 (t, 1H), 7.2 (d, 1H), 2.5 (s, 3H).

Sources & evidence

ORD record
ord-8579e40f71524fd5af916c4a48fa7d8b
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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