2-Amino-2-methyl-1,3-propanediol → N,N'-bis-(1,3-dihydroxy-2-methylprop-2-yl)pyrazine-2,3-dicarboxamide

HRID 1954844Notes

Reaction equation

HRID 1954844 reaction equation
C[C:2]1[N:7]=[C:6]([C:8]([O-:10])=O)[C:5]([C:11]([O-:13])=O)=[N:4][C:3]=1C.[NH2:15][C:16]([CH3:21])([CH2:19][OH:20])[CH2:17][OH:18]>C(O)C>[OH:18][CH2:17][C:16]([NH:15][C:8]([C:6]1[C:5]([C:11]([NH:15][C:16]([CH3:21])([CH2:19][OH:20])[CH2:17][OH:18])=[O:13])=[N:4][CH:3]=[CH:2][N:7]=1)=[O:10])([CH3:21])[CH2:19][OH:20]

Participants

4

Reactant 2

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 72007845,6-Dimethylpyrazine-2,3-dicarboxylate

Product 1

HCID 23293754N,N'-bis-(1,3-dihydroxy-2-methylprop-2-yl)pyrazine-2,3-dicarboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyrazine-2,3-dicarboxylic acid (34 mg, 0.2 mmol), PyBOP (229 mg, 0.44 mmol), HOBt (60 mg, 0.44 mmol) and NMM (0.7 mL, 0.64 mmol) were dissolved in DMF (2 mL) and allowed to react for 10 min. 2-Amino-2-methyl-1,3-propanediol (46 mg, 0.44 mmol) was then added and stirring was continued overnight. The entire reaction mixture was then fractionated on a RP-HPLC column (Vydac 218TP1022, 22×250 mm, 10 mL/min, 0 to 15% MeCN in 0.1% aq CF3COOH over 40 min). Appropriate fractions were pooled, rechromatographed and lyophilised to yield the pure title compound. Alternatively, the title compound was synthesised as follows: dimethylpyrazine-2,3-dicarboxylate (1.5 g, 7.7 mmol) and 2-amino-2-methyl-1,3-propanediol (1.6 g, 15.4 mmol) in absolute ethanol (5 mL) were heated under reflux during 4 hours. The reaction mixture was then cooled and the solvent was removed under reduced pressure. The residue was chromatographed on a flash silica gel column using CHCl3 /MeOH (4:1) as the eluant. Solvents were removed in vacua and the pure title compound (2.2 g, 85%) was obtained after recrystallisation from isopropanol/hexane.

Workup

  1. customAlternatively, the title compound was synthesised
  2. temperatureunder reflux during 4 hours
  3. temperatureThe reaction mixture was then cooled
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was chromatographed on a flash silica gel column
  6. customSolvents were removed in vacua

Sources & evidence

ORD record
ord-e6db920185524617922b804e92d5c60d
Source dataset
uspto-grants-2000_09
Patent number
US06124298

Reaction notes

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