Cyanoacetic acid → HCID 19071304, compound

HRID 1955644Notes

Reaction equation

HRID 1955644 reaction equation
[C:1]([CH2:3][C:4](O)=[O:5])#[N:2].[CH:7]1([CH2:13][NH:14][C:15]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[S:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C(OC(=O)C)(=O)C>[NH2:2][C:1]1[N:14]([CH2:13][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[C:15](=[S:16])[N:17]([CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:4](=[O:5])[CH:3]=1

Participants

4

Reactant 2

HCID 9740Cyanoacetic acidHCID 19071297HCID 19071297, compound

Product 1

HCID 19071304HCID 19071304, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of cyanoacetic acid (Aldrich, 1.23 g, 14.3 mmol) and 1,3-bis(cyclohexylmethyl)thiourea (from step (a), 3.50 g, 13.0 mmol) in acetic anhydride (8.1 mL) was stirred at 70° C. for 2 h under nitrogen. Volatiles were removed in vacuo and the residual oil was dried by evaporation of portions of 10% water-ethanol (3×50 mL). The resulting solids were dissolved in ethanol (12 mL)-water (28 mL) at reflux with adjustment of the pH to 11 by addition of 10% aqueous sodium carbonate. After 1 h, the mixture was cooled to ambient temperature, volatiles were removed under vacuum, and the residue was chromatographed on silica gel. 6-Amino-1,3-bis(cyclohexylmethyl)-1,2-dihydro-2-thioxo-4(3H)-pyrimidinone eluted with 4% methanol in chloroform, and was recrystallized from 2% ethyl acetate in hexanes to provide an off-white powder (2.27 g, 50%), m.p. 147°-150° C.; 1H-NMR (DMSO-d6) consistent with structure.

Workup

  1. customVolatiles were removed in vacuo
  2. dry with materialthe residual oil was dried by evaporation of portions of 10% water-ethanol (3×50 mL)
  3. dissolutionThe resulting solids were dissolved in ethanol (12 mL)-water (28 mL)
  4. temperatureat reflux with adjustment of the pH to 11 by addition of 10% aqueous sodium carbonate
  5. customvolatiles were removed under vacuum
  6. customthe residue was chromatographed on silica gel
  7. wash6-Amino-1,3-bis(cyclohexylmethyl)-1,2-dihydro-2-thioxo-4(3H)-pyrimidinone eluted with 4% methanol in chloroform
  8. customwas recrystallized from 2% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-edeed6e67a0c4faa991be796af3f26d9
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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