Cyanoacetic acid → 6-Amino-1,3-bis(cyclohexylmethyl)uracil

HRID 1955619Notes

Reaction equation

HRID 1955619 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)=[O: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](=[O: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 2315151,3-Bis(cyclohexylmethyl)urea

Product 1

HCID 222449716-Amino-1,3-bis(cyclohexylmethyl)uracilYield 94.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

Cyanoacetic acid (Aldrich, 21.0 g, 0.247 mole) was dissolved in acetic anhydride (260 mL). This solution was added to 1,3-bis(cyclohexylmethyl)urea (from step (a), 54.5 g, 0.216 mole) and the solution maintained at 80° C. for 2 h under nitrogen. Volatiles were removed in vacuo and the residual oil dried by evaporation of portions of 10% water-ethanol (3×400 mL). The residual solids were dissolved in ethanol (600 mL)-water(300 mL) at 80° C. with adjustment of the pH to 10 by addition of 10% aqueous sodium carbonate. The hot solution was diluted with water (75 mL) and cooled to ambient temperature. The colorless crystals which formed were filtered off, washed with water (3×500 mL) and dried at 0.5 Torr to give 6-amino-1,3-bis(cyclohexylmethyl)uracil (64.98 g, 94%), m.p. 138°-141° C.;

Workup

  1. customVolatiles were removed in vacuo
  2. dry with materialthe residual oil dried by evaporation of portions of 10% water-ethanol (3×400 mL)
  3. dissolutionThe residual solids were dissolved in ethanol (600 mL)-water(300 mL) at 80° C. with adjustment of the pH to 10
  4. additionby addition of 10% aqueous sodium carbonate
  5. additionThe hot solution was diluted with water (75 mL)
  6. temperaturecooled to ambient temperature
  7. customThe colorless crystals which formed
  8. filtrationwere filtered off
  9. washwashed with water (3×500 mL)
  10. customdried at 0.5 Torr

Sources & evidence

ORD record
ord-27040492c6cf4adc925f40e165703512
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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