Ethyl cyanoacetate → 6-Amino-1-(cyclopropylmethyl)-2,3-dihydro-2-thioxo-4(1H)-pyrimidinone

HRID 31063Notes

Reaction equation

HRID 31063 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]([NH2:8])=[S:7])[CH2:3][CH2:2]1.C[O-].[Na+].[C:12]([CH2:14][C:15](OCC)=[O:16])#[N:13]>C(O)C>[NH2:13][C:12]1[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6](=[S:7])[NH:8][C:15](=[O:16])[CH:14]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 2795339N-CyclopropylmethylthioureaHCID 10942334Sodium Methoxide

Product 1

HCID 866010556-Amino-1-(cyclopropylmethyl)-2,3-dihydro-2-thioxo-4(1H)-pyrimidinoneYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1-cyclopropylmethyl-2-thiourea (0.60 g, 4.6 mmol) in ethanol (10 mL) was added sodium methoxide (0.26 g, 4.8 mmol) and, after 5 minutes, ethyl cyanoacetate (0.50 mL, 4.6 mmol). The resulting mixture was heated to reflux for 2 h and 40 minutes followed by evaporation of the solvent under reduced pressure and treatment of the resulting yellow solid with 2M aqueous acetic acid (10 mL) giving a white solid. The solid was collected by filtration and washed with 2M aqueous acetic acid (10 mL), stirred with ethanol (10 mL) followed by evaporation and drying under reduced pressure, giving the title compound (0.51 g, 56%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h and 40 minutes
  3. customfollowed by evaporation of the solvent under reduced pressure and treatment of the resulting yellow solid with 2M aqueous acetic acid (10 mL)
  4. customgiving a white solid
  5. filtrationThe solid was collected by filtration
  6. washwashed with 2M aqueous acetic acid (10 mL)
  7. customfollowed by evaporation
  8. customdrying under reduced pressure

Sources & evidence

ORD record
ord-2e78d71160104c28a4a102b782dcc95d
Source dataset
uspto-grants-2008_09
Patent number
US07425560B2

Reaction notes

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