Triethylamine → 3-Amino-5-(2-methoxy-ethylamino)-6-trimethylsilanylethynyl-pyrazine-2-carboxylic acid methyl ester

HRID 474126Notes

Reaction equation

[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].CCN(CC)CC.[CH3:14][O:15][C:16]([C:18]1[C:23]([NH2:24])=[N:22][C:21]([NH:25][CH2:26][CH2:27][O:28][CH3:29])=[C:20](Br)[N:19]=1)=[O:17].COC(C1C(N)=NC(NCCOC)=C(Cl)N=1)=O>C1COCC1.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.[Cu]I>[CH3:14][O:15][C:16]([C:18]1[C:23]([NH2:24])=[N:22][C:21]([NH:25][CH2:26][CH2:27][O:28][CH3:29])=[C:20]([C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4])[N:19]=1)=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethynyl-trimethyl-silane (1.05 g, 10.7 mmol), bis(triphenylphosphine)palladium(II) chloride (150 mg, 0.214 mmol), Copper(I) iodide (41 mg, 0.214 mmol) and NEt3 (2.09 ml, 14.98 mmol) in THF (17 ml) was added under an argon atmosphere a mixture (about 1:1) of 3-amino-6-bromo-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl ester and 3-amino-6-chloro-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl ester (651 mg, 2.14 mmol) and the mixture was heated to 80° C. for 17 h. The reaction mixture was filtered through Hyflo and the solvent evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 60:40) to provide the title compound as brown solid.

Workup

filtrationThe reaction mixture was filtered through Hyflo
customthe solvent evaporated
customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 60:40)

Sources & evidence

ORD record: ord-3ded998ffff14ad3bff0e5fe9b7ef649
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637508B2

Reaction notes

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