Iodine → 6-amino-3-benzyl-1-butyl-1H-pyrimidine-2,4-dione

HRID 720606Notes

Reaction equation

HRID 720606 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[C:6](=[O:12])[NH:5][C:4](=[O:13])[CH:3]=1.C[Si](C)(C)N[Si](C)(C)C.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.II>S([O-])([O-])(=O)=O.[NH4+].[NH4+].CO>[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[C:6](=[O:12])[N:5]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:4](=[O:13])[CH:3]=1

Participants

7

Reactant 4

HCID 807IodineHCID 7498Benzyl BromideHCID 13838Hexamethyldisilazane2×HCID 24289966-Amino-1-butyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 218918436-amino-3-benzyl-1-butyl-1H-pyrimidine-2,4-dioneYield 39.8%

Reagents, catalysts & solvents 2

HCID 6097028Ammonium SulfateCatalystHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

6-Amino-1-butyl-1H-pyrimidine-2,4-dione (1.72 g, 9.4 mmol), 1,1,1,3,3,3-hexamethyldisilazane (30 mL), and ammonium sulfate (0.03 g, 0.2 mmol) were heated under nitrogen at reflux for 24 h. After cooling to room temperature the 1,1,1,3,3,3-hexamethyldisilazane was removed under vacuum to give a light brown oil to which was added benzylbromide (1.1 mL, 1.58 g, 9.2 mmol) and a crystal of iodine. The resulting mixture was heated in a 110° C. oil bath for 1 h. The mixture was cooled in as ice bath while methanol was cautiously added. After concentration and trituration with chloroform and cooling to −20° C. freezer, the solid product was isolated by filtration. This material was passed through a pad of silica gel 60 (35–70 mesh) eluted with 9:1 chloroform/methanol to give 1.0 g of pure 6-amino-3-benzyl-1-butyl-1H-pyrimidine-2,4-dione. LRMS, m/z(M+H)=274.4.

Workup

  1. temperatureat reflux for 24 h
  2. customwas removed under vacuum
  3. customto give a light brown oil to which
  4. additionwas cautiously added
  5. concentrationAfter concentration and trituration with chloroform
  6. temperaturecooling to −20° C. freezer
  7. customthe solid product was isolated by filtration
  8. washeluted with 9:1 chloroform/methanol

Sources & evidence

ORD record
ord-01a47002def2498e94215607ae91f4c7
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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