Sodium Hydroxide → 3-Amino-5-tert-butylselenophene-2-carboxamide

HRID 2408946Notes

Reaction equation

HRID 2408946 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[Se:4][C:3]=1[C:11]#[N:12].[OH-:13].[Na+]>C(O)C>[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:9])([CH3:8])[CH3:10])[Se:4][C:3]=1[C:11]([NH2:12])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 595472203-Amino-5-(tert-butyl)selenophene-2-carbonitrile

Product 1

HCID 866468893-Amino-5-tert-butylselenophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As shown in scheme L, 3-amino-5-(tert-butyl)selenophene-2-carbonitrile is treated with 10% aqueous NaOH solution/ethanol to give 3-amino-5-(tert-butyl)selenophene-2-carboxamide. Which is cyclised using formic acid/sulfuric acid to give 6-(tert-butyl)-3-hydroselenopheno[3,2-d]pyrimidin-4-one and further treatment with thionyl chloride gave 6-(tert-butyl)-4-chloroselenopheno[3,2-d]pyrimidine (Hesse, S. et. al., Synthesis, 2009, 1204-1208) in good yield. Treatment of this 4-chlorocompound with 3-amino-5-tert-butylselenophene-2-carboxamide in the presence of DMF/NaOH gave 5-(tert-butyl)-3-{[6-(tert-butyl)selenopheno[2,3-e]pyrimidin-4-yl]amino}selenophene-2-carboxamide.

Sources & evidence

ORD record
ord-74e3a7050d24415eb1ce41075dd245df
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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