Sodium Hydroxide → 3-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

HRID 1959340Notes

Reaction equation

HRID 1959340 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:13]=[C:14]3[C:19](=[N:20][CH:21]=2)[N:18]=CN(C)[C:15]3=[O:23])[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[OH-:24].[Na+]>CO>[NH2:18][C:19]1[C:14]([C:15]([OH:23])=[O:24])=[N:13][C:12]([N:9]2[CH2:8][CH2:7][N:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH2:11][CH2:10]2)=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66744532HCID 66744532, compound

Product 1

HCID 667445273-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazine-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-(4-ethylsulfonylpiperazin-1-yl)-3-methyl-pteridin-4-one (5 g, 14.78 mmol) in methanol (51.00 mL) was treated with sodium hydroxide (45.92 mL of 10% w/v, 114.8 mmol) and the reaction mixture stirred at RT overnight. The reaction mixture was concentrated in vacuo and the residue diluted with water and neutralised with formic acid. The resulting precipitate was filtered off and the filtrate acidified to pH4 by the addition of formic acid and extracted with dichloromethane. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo to give the product as a bright yellow solid (4.66 g, 52% Yield). 1H NMR (400.0 MHz, CDCl3) d 1.45 (3H, t), 3.05 (2H, q), 3.54 (8H, m), 6.05 (2H, br s), 8.21 (1H, s) ppm; MS (ES+) 316

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue diluted with water and neutralised with formic acid
  3. filtrationThe resulting precipitate was filtered off
  4. additionthe filtrate acidified to pH4 by the addition of formic acid
  5. extractionextracted with dichloromethane
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f5efa72e3464bf4b363784aa0d36d74
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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