Ammonium Chloride → HCID 71271064, compound

HRID 1752500Notes

Reaction equation

HRID 1752500 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].[Cl-].[Li+].C([Sn](CCCC)(CCCC)/[CH:20]=[CH:21]\[O:22][CH2:23][CH3:24])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](/[CH:20]=[CH:21]\[O:22][CH2:23][CH3:24])=[CH:7][N:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 5706773cis-1-Ethoxy-2-(tri-n-butylstannyl)ethyleneHCID 53417426Methyl 3-amino-5-chloropyrazine-2-carboxylate

Product 1

HCID 71271064HCID 71271064, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-amino-5-chloro-pyrazine-2-carboxylic acid methyl ester [28643-16-5] (2 g, 10.66 mmol), lithium chloride (1.582 g, 37.3 mmol), Pd(PPh3)2Cl2 (0.748 g, 1.066 mmol) and tributyl-((Z)-2-ethoxy-vinyl)-stannane (6.42 ml, 19.19 mmol) in DMF (104 ml) under argon was heated at 80° C. bath temperature for 1.5 h. A saturated. aq. NH4Cl was added and the mixture was extracted with MTBE, then once with EtOAc/THF 3/1. The combined organic layer was 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 1:9) to provide the title compound as yellow oil (1.96 g).

Workup

  1. extractionthe mixture was extracted with MTBE
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:9)

Sources & evidence

ORD record
ord-819a9b1a547d4468bb9fe818fd8351be
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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