Ethyl cyanoacetate → 6-amino-1-(pyridin-3-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 912649Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([NH2:11])=[S:10])[CH:2]=1.[C:12]([CH2:14][C:15](OCC)=[O:16])#[N:13]>>[NH2:13][C:12]1[N:8]([CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:9](=[S:10])[NH:11][C:15](=[O:16])[CH:14]=1

Participants

Reactant 2

HCID 7764Ethyl cyanoacetate

HCID 28265651-(Pyridin-3-ylmethyl)thiourea

Product 1

HCID 49033196-amino-1-(pyridin-3-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 83%

Procedure

The title compound was prepared in accordance with the general method described in Example 1(b) using N-(pyridin-3-ylmethyl)thiourea (Beaudegnies, R., Wendeborm, S., Heterocycles, 2003, 11, 2417-2424) (1.19 g, 7.12 mmol) and ethyl cyanoacetate (0.97 g, 8.54 mmol), giving the title compound (1.38 g, 83%) as a solid.

Workup

customThe title compound was prepared in accordance with the general method

Sources & evidence

ORD record: ord-eebf34022043437fba30b5f8fbf323a4
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026244B2

Reaction notes

Loading…