Sodium Methoxide → HCID 178467322, compound

HRID 241773Notes

Reaction equation

HRID 241773 reaction equation
CO[C:3]([C:5]1[C:10]([NH:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].C[O-].[Na+]>CO>[OH:17][C:12]1[C:13]([C:14](=[O:16])[CH3:15])=[C:3]([OH:4])[C:5]2[C:10]([N:11]=1)=[N:9][CH:8]=[CH:7][N:6]=2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 581149193-(3-Oxo-butyrylamino)-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 178467322HCID 178467322, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-(3-Oxo-butyrylamino)-pyrazine-2-carboxylic acid methyl ester (Example 6.1) (15 g) in methanol (80 ml) was added to a suspension of sodium methoxide (7.2 g) in methanol (80 ml). The suspension was heated to reflux for 2 hours and then stored for 16 hours at ambient temperature. The mixture was filtered and the filtrate was acidified to pH 1 by addition of concentrated hydrochloric acid (36% by weight in water) and then filtered again. The solid was washed with water and then diethyl ether to give 1-(6,8-dihydroxy-pyrido[2,3-b]pyrazin-7-yl)-ethanone (10.1 g). 1H-NMR (400 MHz, d6-DMSO): 2.70 (s, 3H), 8.60 (d, 1H), 8.71 (d, 1H), 12.2 (s, 1H), 16.25 (s, 1H) ppm.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was acidified to pH 1 by addition of concentrated hydrochloric acid (36% by weight in water)
  5. filtrationfiltered again
  6. washThe solid was washed with water

Sources & evidence

ORD record
ord-8e26486ec90d4f1694998fc5167c62ef
Source dataset
uspto-grants-2014_02
Patent number
US08653078B2

Reaction notes

Loading…