Ethyl cyanoacetate → 6-Amino-1-[(3-isopropylisoxazol-5-yl)methyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 912690Notes

Reaction equation

HRID 912690 reaction equation
[CH:1]([C:4]1[CH:8]=[C:7]([CH2:9][NH:10][C:11]([NH2:13])=[S:12])[O:6][N:5]=1)([CH3:3])[CH3:2].[O-]CC.[Na+].[C:18]([CH2:20][C:21](OCC)=[O:22])#[N:19]>>[NH2:19][C:18]1[N:10]([CH2:9][C:7]2[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:8]=2)[C:11](=[S:12])[NH:13][C:21](=[O:22])[CH:20]=1

Participants

4

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 86631131HCID 86631131, compound

Product 1

HCID 866311326-Amino-1-[(3-isopropylisoxazol-5-yl)methyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 14%

Procedure

The title compound was prepared in accordance with the general method described in Example 12(b) by using 1-[(3-isopropylisoxazol-5-yl)methyl]thiourea (1.11 g, 5.55 mmol, obtained from Example 15(a)), sodium ethoxide (21% w/v, 5.4 mL, 16.7 mmol) and ethyl cyanoacetate (1.8 mL, 16.7 mmol) with the exception that the reaction time after completed addition was 2 h. This provided 0.20 g (14% yield) of the title compound.

Workup

  1. customThe title compound was prepared in accordance with the general method
  2. additionaddition

Sources & evidence

ORD record
ord-a6e26bad7ce345a79ba657359e82bfda
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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