Methanol → 3-Amino-6-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

HRID 1959357Notes

Reaction equation

HRID 1959357 reaction equation
CN1[C:11](=[O:12])[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[N:9]=2)[N:4]=C1.C[OH:27]>[OH-].[Na+]>[NH2:4][C:5]1[C:10]([C:11]([OH:27])=[O:12])=[N:9][C:8]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:15][CH2:14]2)=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 66745135Tert-butyl 4-(3-methyl-4-oxo-3,4-dihydropteridin-6-yl)piperazine-1-carboxylate

Product 1

HCID 667448533-Amino-6-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acidYield 34%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Tert-butyl 4-(3-methyl-4-oxo-pteridin-6-yl)piperazine-1-carboxylate (25 g, 72.17 mmol) was stirred in NaOH (250 mL of 10% w/w,) and MeOH (250 mL) overnight at RT. The resulting suspension was concentrated and then acidified with formic acid followed by extraction of the aqueous with DCM. The mixture was treated with water, taken to pH 10 and filtered. The aqueous layer was reacidified and the resulting precipitated product was extracted into DCM and concentrated to give the product as a yellow solid (8 g, 24.74 mmol, 34% Yield).

Workup

  1. customat RT
  2. concentrationThe resulting suspension was concentrated
  3. extractionfollowed by extraction of the aqueous with DCM
  4. additionThe mixture was treated with water
  5. filtrationfiltered
  6. customthe resulting precipitated product
  7. extractionwas extracted into DCM
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f4b3f02a7da4447a86571d57bc2c52dc
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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