Ethanol → HCID 178519436, compound

HRID 396272Notes

Reaction equation

HRID 396272 reaction equation
[CH:1]1([CH2:7][N:8]2[C:15]([NH2:16])=[C:14]([NH2:17])[C:12](=[O:13])[N:11]([CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:9]2=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.II.[O-]S([O-])(=S)=O.[Na+].[Na+].[CH2:34]([OH:36])[CH3:35]>>[CH:19]1([CH2:18][N:11]2[C:12](=[O:13])[C:14]3[N:17]=[C:7]([C:1]4[CH:6]=[CH:5][C:35]([CH:34]=[O:36])=[CH:3][CH:2]=4)[NH:16][C:15]=3[N:8]([CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:9]2=[O:10])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 702EthanolHCID 807IodineHCID 24477Sodium ThiosulfateHCID 222449751,3-Bis(cyclohexylmethyl)-5,6-diaminouracil

Product 1

HCID 178519436HCID 178519436, compoundYield 82%

Procedure

1,3-Bis(cyclohexylmethyl)-5,6-diaminouracil (143.5 mmol) was freshly prepared as described in Example 1d and dissolved in absolute ethanol (1 L). Terepthaldehyde monodiethylacetal (Aldrich, 28.54 ml, 143.5 mmol) was added and the solution was stirred at room temperature for 3h. The reaction mixture was concentrated at reduced pressure. and residual ethanol was removed by evaporation from dimethoxyethane (400 ml). The resulting yellow solid was dissolved in dimethoxyethane (1 L) and iodine crystals (40.06 g, 157.85 mmol) were added. The reaction mixture was stirred at 50° C. for 4 h and at room temperature overnight. Saturated Na2S2O3 (300 ml) was added and the dimethoxyethane was removed at reduced pressure. The resulting solid was collected by filtration and combined with methanol (300 ml), H2O (100 ml) and conc. Hydrochloric acid (3 ml). After heating at reflux for ten minutes, the solids were collected by filtration and dried to provide the title compound as a tan solid (53.05 g, 82% yield). 1H-NMR (400 MHz, DMSO-d6) δ: 14.13 (s, 1H), 10.05 (s, 1H), 8.31 (d, J=8.2 Hz, 2H), 8.03 (d, J=8.2 Hz, 2H), 3.91 (br d, J=7 Hz, 2H), 3.77 (br d, J=7 Hz, 2H), 1.93 (m, 1H), 1.74 (m, 1H), 1.60 (m, 10H), 1.20-0.90 (m, 10H). MS (ES−): 447 (M−1).

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. customand residual ethanol was removed by evaporation from dimethoxyethane (400 ml)
  3. dissolutionThe resulting yellow solid was dissolved in dimethoxyethane (1 L)
  4. stirringThe reaction mixture was stirred at 50° C. for 4 h and at room temperature overnight
  5. customthe dimethoxyethane was removed at reduced pressure
  6. filtrationThe resulting solid was collected by filtration
  7. temperatureAfter heating
  8. temperatureat reflux for ten minutes
  9. filtrationthe solids were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-ae0445d0e35747e9bde56b14f8f485be
Source dataset
uspto-grants-2003_08
Patent number
US06608069B1

Reaction notes

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