Acetic Acid → 6-Amino-1-pentyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 2368544Notes

Reaction equation

HRID 2368544 reaction equation
[CH2:1]([NH:6][C:7]([NH2:9])=[S:8])[CH2:2][CH2:3][CH2:4][CH3:5].[C:10]([CH2:12][C:13](OCC)=[O:14])#[N:11].[O-]CC.[Na+].C(O)(=O)C>C(O)C.O>[NH2:11][C:10]1[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7](=[S:8])[NH:9][C:13](=[O:14])[CH:12]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 6451284Urea, 1-pentyl-2-thio-

Product 1

HCID 576001846-Amino-1-pentyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 65.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

N-Pentylthiourea (10.0 g, 0.068 mol) was mixed with ethyl cyanoacetate (9.3 g, 0.082 mol) and sodium ethoxide (6.4 g, 0.094 mol) in ethanol (60 mL). The mixture was stirred at 75° C. overnight. After cooling, a solution of 10% acetic acid in water (150 mL) was added. The solid formed was collected by filtration and washed with water to afford the desired product (9.5 g, 65% yield). LCMS calculated for C9H16N3OS: (M+H) 214.1. Found 214.1.

Workup

  1. temperatureAfter cooling
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-c9e1f289d6714e0aa816f517c325f793
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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