Methyl 3-aminopyrazinecarboxylate → 3-(3-Oxo-butyrylamino)-pyrazine-2-carboxylic acid methyl ester

HRID 241772

Reaction equation

HRID 241772 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].CC1(C)[O:18][C:17](=O)[CH:16]=[C:15]([CH3:20])[O:14]1>>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:17](=[O:18])[CH2:16][C:15](=[O:14])[CH3:20])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 72669Methyl 3-aminopyrazinecarboxylateHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 581149193-(3-Oxo-butyrylamino)-pyrazine-2-carboxylic acid methyl ester

Procedure

3-Aminopyrazine-2-carboxylic acid methyl ester (12 g) and 2,2,6-trimethyl-[1,3]dioxin-4-one (15.6 ml) were heated to reflux for 6 hours. The reaction mixture was concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 4:1, then ethyl acetate) to give 3-(3-oxo-butyrylamino)-pyrazine-2-carboxylic acid methyl ester as a beige solid (15 g). 1H-NMR (400 MHz, CDCl3): 2.33 (s, 3H), 3.91 (s, 2H), 4.05 (s, 3H), 8.40 (d, 1H), 8.51 (d, 1H), 10.06 (s, 1H) ppm.

Workup

  1. temperatureto reflux for 6 hours
  2. concentrationThe reaction mixture was concentrated
  3. customThe residue was purified by column chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-f18e11a35c154cef83d2e1cfeaec1130
Source dataset
uspto-grants-2014_02
Patent number
US08653078B2

Linked notes

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