Diiodomethane → Methyl 3-iodopyrazine-2-carboxylate

HRID 1896678Notes

Reaction equation

HRID 1896678 reaction equation
N(OCCC(C)C)=O.[CH3:9][O:10][C:11]([C:13]1[C:18](N)=[N:17][CH:16]=[CH:15][N:14]=1)=[O:12].[I:20]CI>>[CH3:9][O:10][C:11]([C:13]1[C:18]([I:20])=[N:17][CH:16]=[CH:15][N:14]=1)=[O:12]

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 72669Methyl 3-aminopyrazinecarboxylate

Product 1

HCID 57681180Methyl 3-iodopyrazine-2-carboxylateYield 44%

Conditions

Temperature
100 °C

Procedure

Isoamyl nitrite (5.2 mL, 39 mmol) was added to a suspension of 3-aminopyrazine-2-carboxylic acid methyl ester (1.9 g, 12 mmol) in diiodomethane (20 mL) at 85° C., then the mixture was stirred at 100° C. for 15 hours. The reaction mixture was allowed to stand and purified by silica gel column chromatography to give 1.4 g of the title reference compound as a pale yellow solid. (Yield 44%)

Workup

  1. custompurified by silica gel column chromatography
  2. customto give 1.4 g of the title reference compound as a pale yellow solid

Sources & evidence

ORD record
ord-def8298dd9734fd5a45c532b17d80ba0
Source dataset
uspto-grants-2013_08
Patent number
US08518973B2

Reaction notes

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