Water → HCID 68110364, compound

HRID 1752485Notes

Reaction equation

HRID 1752485 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8](Cl)=[CH:7][N:6]=1)=[O:4].[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC.[Cl-].[Li+].O>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([CH:13]=[CH2:14])=[CH:7][N:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 53417426Methyl 3-amino-5-chloropyrazine-2-carboxylate

Product 1

HCID 68110364HCID 68110364, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 3-amino-5-chloro-pyrazine-2-carboxylic acid methyl ester (GB 1248146, 161 mg 0.86 mmol), tributyl(vinyl)tin (0.352 ml, 1.204 mmol) and lithium chloride (102 mg, 2.498 mmol) in DMF (4 ml) was added PdCl2(PPh3)2 (30.2 mg, 0.043 mmol) and the mixture was heated to 85° C. for 2.5 h. After cooling to room temperature water was added and the mixture was extracted with EtOAc, the combined organic layers were washed with water and half saturated aq. NaCl, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:9) to provide the title compound as yellow solid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with water and half saturated aq. NaCl
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:9)

Sources & evidence

ORD record
ord-5d0db4964ef7432bb2f515f7c8c08628
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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