Formic Acid → Methyl 3,5-diaminopyrazine-2-carboxylate

HRID 2079978Notes

Reaction equation

HRID 2079978 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([NH2:12])=[C:7](Cl)[N:6]=1)=[O:4].C(O)=O.C(N(CC)CC)C>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([NH2:12])=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 73827Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

Product 1

HCID 15148126Methyl 3,5-diaminopyrazine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid methyl ester (8.00 g, 39.5 mmol) in tetrahydrofuran (150 mL) were added tetrakis(triphenylphosphine)palladium(0) (2.28 g, 1.98 mmol), formic acid (2.24 mL, 59.3 mmol) and triethylamine (16.5 mL, 119 mmol) at 0° C. under nitrogen atmosphere, then, the solution was stirred at 125° C. for 12 hours. The reaction solution was cooled to room temperature, and a solid precipitated. This solid was collected by filtration, and the title compound (10.7 g, quantitatively) was obtained as a crude product of a white solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customa solid precipitated
  3. filtrationThis solid was collected by filtration

Sources & evidence

ORD record
ord-863f31c5e91346e28b8c99dfca38986d
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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