Cesium carbonate → 6-Methyl-3-(pyridin-3-ylamino)-pyrazine-2-carboxylic acid ethyl ester

HRID 550588Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[N:10][CH:9]=[C:8]([CH3:13])[N:7]=1)=[O:5])[CH3:2].I[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH:12][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:10][CH:9]=[C:8]([CH3:13])[N:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

3-Amino-6-methyl-pyrazine-2-carboxylic acid ethyl ester (Example C) (800 mg, 4.4 mmol) and 3-iodopyridine (1.63 g, 8.0 mmol) were dissolved in 17 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (510 mg, 0.88 mmol), cesium carbonate (2.30 g, 7.0 mmol) and tri(dibenzylideneacetone)dipalladium chloroform complex (460 mg, 0.44 mmol) were added and the reaction mixture was stirred for 16 hours at 130° C. The reaction mixture was then evaporated and purified by flash chromatography on silica gel (heptane/ethyl acetate 9:1->heptane/ethyl acetate 1:2). The desired product was obtained as a yellow oil (455 mg, 40%), MS: m/e=259.2 (M+H+).

Workup

customThe reaction mixture was then evaporated
custompurified by flash chromatography on silica gel (heptane/ethyl acetate 9:1->heptane/ethyl acetate 1:2)

Sources & evidence

ORD record: ord-e4be2f012d06418ca75b4f89633cef36
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947685B2

Reaction notes

Loading…