Sodium Hydroxide → 6-Amino-1,3-dibutyluracil

HRID 965186Notes

Reaction equation

HRID 965186 reaction equation
[C:1]([CH2:3][C:4]([N:6]([CH2:14][CH2:15][CH2:16][CH3:17])[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])=[O:5])#[N:2].[OH-].[Na+]>CO>[CH2:10]([N:9]1[C:1]([NH2:2])=[CH:3][C:4](=[O:5])[N:6]([CH2:14][CH2:15][CH2:16][CH3:17])[C:7]1=[O:8])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10376972N-(2-cyanoacetyl)-N,N'-dibutylurea

Product 1

HCID 99918436-Amino-1,3-dibutyluracilYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N-Di-n-butylurea (34.45 g, 0.2 mmol), cyanoacetic acid (19.56 g, 0.23 mol), and acetic anhydride (81.66 ml, 0.8 mol) were heated at 80° C. for 2 h under nitrogen and solvent was removed by rotary evaporation to yield N-(2-cyanoacetyl)-N,N'-dibutylurea. The N-(2-cyanoacetyl)-N,N'-dibutylurea was dissolved in methanol (100 ml) and 4N NaOH (100 ml) was added. The reaction mixture was cooled for 30 min with stirring and the solid was filtered and dried to yield 1,3-di-n-butyl-6-aminouracil (47.04 g, 99.5%) as a colorless solid, m.p. 90.1°-92.4° C.; 1H NMR (DMSO-d6) δ1.72-1.93 (m, 6H, 2×CH3, 1.18-1.33 (m, 4H, 2×CH2), 1.39-1.52 (M, 4H, 2×CH2), 3.70 (t, 2H, N--CH2), 3.76 (t, 2H, N--CH2), 4.64 (s, 1H, H-4), 6.77 (br s, exchangeable with D2O, 2H, NH2).

Workup

  1. temperatureThe reaction mixture was cooled for 30 min
  2. filtrationthe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-1e5b46dee08a4ed3abc1d30f4e634eca
Source dataset
uspto-grants-1998_06
Patent number
US05773423

Reaction notes

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