Potassium Carbonate → HCID 56952134, compound

HRID 705029Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:8][CH:9]=[CH:10][N:11]=2)[CH:2]=1.Br[C:13]1[N:18]=[C:17]([C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:8][C:9]([C:13]3[N:18]=[C:17]([C:19]4[N:20]=[CH:21][CH:22]=[CH:23][N:24]=4)[CH:16]=[CH:15][CH:14]=3)=[CH:10][N:11]=2)[CH:2]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Under argon, 130 mg (0.88 mmol) of 2-(3-pyridinyl)oxazole (Hel. Chim. Acta 1962, 42, 375-381), 175 mg (0.74 mmol) of 2-(6-bromo-2-pyridyl)pyrimidine, 11 mg (0.02 mmol) of [(t-Bu)2P(OH)]2PdCl2 (POPd) and 205 mg (1.48 mmol) of potassium carbonate were initially charged in 5 ml of N,N-dimethylformamide, and the mixture was stirred at 120° C. for 16 hours. For work-up, the reaction mixture was concentrated under reduced pressure and the crude product that remained was purified by chromatography on silica gel (mobile phase: dichloromethane/methanol). This gave 126 mg (54% of theory) of 2-{6-[2-(pyridin-3-yl)-1,3-oxazol-5-yl]pyridin-2-yl}pyrimidine.

Workup

concentrationFor work-up, the reaction mixture was concentrated under reduced pressure
customthe crude product that remained was purified by chromatography on silica gel (mobile phase: dichloromethane/methanol)

Sources & evidence

ORD record: ord-0367dad47776491fb64b504a490e7b94
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173396B2

Reaction notes

Loading…