Potassium Phosphate, Tribasic → HCID 67299911, compound

HRID 1260301Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7](Br)[N:6]=1)=[O:4].[CH:13]1(B(O)O)[CH2:15][CH2:14]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([CH:13]2[CH2:15][CH2:14]2)[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 3-amino-6-bromopyrazine-2-carboxylic acid methyl ester (17.8 g, 76.7 mmol), cyclopropylboronic acid (8.57 g, 99.7 mmol), potassium phosphate (57.0 g, 268 mmol) and tricyclohexylphosphine (2.15 g, 7.67 mmol) in toluene (445 ml) and water (22 ml) was added palladium(II) acetate (0.86 g, 3.84 mmol). The reaction mixture was heated to 100° C. and stirred for 20 h. Water (200 ml) was added, the organic layer was washed with water and brine and the aqueous layer was back-extracted with ethyl acetate. The combined organic phases were dried and the solvent was evaporated. The product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as yellow solid (1.69 g, 11.4%).

Workup

washthe organic layer was washed with water and brine
extractionthe aqueous layer was back-extracted with ethyl acetate
customThe combined organic phases were dried
customthe solvent was evaporated
customThe product was obtained after silica gel chromatography

Sources & evidence

ORD record: ord-fb2efe452e5c4a9994177c612cff5510
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470820B2

Reaction notes

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