Ammonium Chloride → HCID 86689172, compound

HRID 1752505Notes

Reaction equation

HRID 1752505 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8](Cl)=[C:7]([Cl:13])[N:6]=1)=[O:4].[Cl-].[Li+].C([Sn](CCCC)(CCCC)[C:21]([O:23][CH2:24][CH3:25])=[CH2:22])CCC.[NH4+].[Cl-]>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]([C:21]([O:23][CH2:24][CH3:25])=[CH2:22])=[C:7]([Cl:13])[N:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 73828Methyl 3-amino-5,6-dichloropyrazine-2-carboxylateHCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 86689172HCID 86689172, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-amino-5,6-dichloro-pyrazine-2-carboxylic acid methyl ester [1458-18-0] (600 mg, 2.62 mmol), lithium chloride (389 mg, 9.17 mmol), Pd(PPh3)2Cl2 (184 mg, 0.262 mmol) and tributyl-(1-ethoxy-vinyl)-stannane [97674-02-7] (1.6 ml, 4.50 mmol) in DMF (27 ml) under argon was heated at 80° C. bath temperature for 3 h and 50 min. Saturated aq. NH4Cl was added and the mixture was extracted with MTBE (3×). The combined organic layers were washed with brine, dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 7:3) to provide the title compound as yellow solid (433 mg).

Workup

  1. custom50 min
  2. extractionthe mixture was extracted with MTBE (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 7:3)

Sources & evidence

ORD record
ord-15a36c48b6a6446cb0b5d09784d395aa
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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