Lithium Hydroxide → HCID 11402309, compound

HRID 2242894Notes

Reaction equation

HRID 2242894 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([NH2:19])[C:8]2[N:9]([N:11]=[C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:10]=1)=[O:4].[Li+].[OH-]>CO.C1COCC1>[NH2:19][C:7]1[C:8]2[N:9]([N:11]=[C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[N:6]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11230684HCID 11230684, compound

Product 1

HCID 11402309HCID 11402309, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine-6-carboxylic acid methyl ester (200 mg; see Example 7 above), LiOH (2 M, 1 mL), and MeOH (a few drops) in THF (20 mL) was heated (at around 70° C.) for 30 minutes. The solvent was removed in vacuo and then the residue was triturated with 0.5 N HCl. The product was dried to afford 8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine-6-carboxylic acid as a light yellow solid (128 mg, 67%). 1H NMR (300 MHz, DMSO-d6) δ 6.73(dd, J=3.5, 1.8 Hz, 1H), 7.18(dd, J=3.5, 0.9 Hz, 1H), 7.7(br. s, 2H), 7.94(dd, J=1.8, 0.8 Hz, 1H), 8.68(s, 1H). MS: m/z 246 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated with 0.5 N HCl
  3. customThe product was dried

Sources & evidence

ORD record
ord-c07c509ff7cf4c4883f280cb5546387f
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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