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

HRID 1664501Notes

Reaction equation

HRID 1664501 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-62f686ba8d4a412b84922973a045f5d7
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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