Diisopropylaniline → 5-(4-Amino-3,5-diisopropylbenzyl)uracil

HRID 1589246Notes

Reaction equation

HRID 1589246 reaction equation
Cl.CN([CH2:5][C:6]1[C:7](=[O:13])[NH:8][C:9](=[O:12])[NH:10][CH:11]=1)C.[CH:14]([C:17]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[C:18]=1[NH2:19])([CH3:16])[CH3:15]>C(O)CO>[NH2:19][C:18]1[C:20]([CH:24]([CH3:25])[CH3:26])=[CH:21][C:22]([CH2:5][C:6]2[C:7](=[O:13])[NH:8][C:9](=[O:12])[NH:10][CH:11]=2)=[CH:23][C:17]=1[CH:14]([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 32484DiisopropylanilineHCID 122674355-Dimethylaminomethyluracil Hydrochloride

Product 1

HCID 136090855-(4-Amino-3,5-diisopropylbenzyl)uracil

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 5-dimethylaminomethyluracil hydrochloride (10.28 g, 50.0 mmol) and 2,6-diisopropylaniline (10.64 g, 60.0 mmol) in ethylene glycol (75 mL) was heated for 41/2 hours at 134°-137° C. After cooling, the title compound was filtered, washed with ethanol, and dried (5.55 g, 37%). A second crop was obtained from the mother liquor upon standing (3.24 g, 21.5%). The two crops were combined and recrystallized from methanol to give the purified title compound (5.84 g, 38.8%).

Workup

  1. temperaturewas heated for 41/2 hours at 134°-137° C
  2. temperatureAfter cooling
  3. filtrationthe title compound was filtered
  4. washwashed with ethanol
  5. customdried (5.55 g, 37%)
  6. customA second crop was obtained from the mother liquor
  7. customrecrystallized from methanol
  8. customto give the
  9. custompurified title compound (5.84 g, 38.8%)

Sources & evidence

ORD record
ord-54c58ab2eee24638baac6bd0fabda616
Source dataset
uspto-grants-1986_02
Patent number
US04568744

Reaction notes

Loading…