Potassium Carbonate → HCID 58368051, compound

HRID 1260302Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([CH:12]2[CH2:14][CH2:13]2)[N:6]=1)=[O:4].Br[C:16]1[CH:17]=[N:18][CH:19]=[N:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].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>CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCCC.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:16]2[CH:17]=[N:18][CH:19]=[N:20][CH:21]=2)=[N:9][CH:8]=[C:7]([CH:12]2[CH2:14][CH2:13]2)[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 140 °C

Procedure

A suspension of 3-amino-6-cyclopropylpyrazine-2-carboxylic acid methyl ester (2.17 g, 11.2 mmol), 5-bromopyrimidine (2.5 g, 15.7 mmol), water (425 μl, 23.6 mmol) and potassium carbonate (2.79 g, 20.2 mmol) in o-xylene (43.4 ml) was vented with argon and treated with ultrasound for 2 min. Palladium(II) acetate (101 mg, 0.45 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 325 mg, 0.56 μmol) were consecutively added under inert gas atmosphere and the reaction mixture was heated to 140° C. and stirred for 2 h. After cooling-down to ambient temperature, the reaction mixture was poured into water (100 ml) and extracted with ethyl acetate. The organic layers were dried and concentrated in vacuo. The product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as yellow solid (2.49 g, 81.7%).

Workup

additiontreated with ultrasound for 2 min
extractionextracted with ethyl acetate
customThe organic layers were dried
concentrationconcentrated in vacuo
customThe product was obtained after silica gel chromatography

Sources & evidence

ORD record: ord-b8ee954cc20543bf8af43534c8603a7c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470820B2

Reaction notes

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