Potassium Hydroxide → 6-Butoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid

HRID 639317

Reaction equation

HRID 639317 reaction equation
[CH2:1]([O:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[N:7][C:6]=1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:2][CH3:3].[CH3:19]OC(C1C=NC(Cl)=C(Br)N=1)=O.N1CCCC1.[OH-].[K+]>C(O)CCC>[CH2:1]([O:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[N:7][C:6]=1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:2][CH2:3][CH3:19]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 31268PyrrolidineHCID 59254839Methyl 6-bromo-5-chloro-2-pyrazinecarboxylateHCID 685674456-Propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid

Product 1

HCID 685703296-Butoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acidYield 8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In analogy to the procedure described for the synthesis of 6-propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid (example 10, step c), the title compound was synthesized from 6-Bromo-5-chloro-pyrazine-2-carboxylic acid methyl ester, butanol (commercially available), pyrrolidine (commercially available) and subsequent saponification with KOH in 8% yield. m/z (ES+): 266.0 (M+H).

Sources & evidence

ORD record
ord-aadca6814f8b46359cb2f69174fd6e96
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Linked notes

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