N-bromobutanimide → 6-Amino-5-bromo-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
Reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[NH:5][C:4](=[O:10])[CH:3]=1.[Br:11]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[NH:5][C:4](=[O:10])[C:3]=1[Br:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 6-amino-1-methyluracil (14.0 g, 100 mmol), N-bromosuccinimide (21.0 g, 118 mmol), and dry DMF (250 mL) was heated at 80° C. for 3 h. The reaction mixture was evaporated in vacuo and the residue was slurried with ice-cold 50% aqueous ethanol (150 mL) and filtered. The resulting off-white solid was washed with ethanol, then ether and dried to yield 18.0 g 2a (83%). mp 274° C. dec; UV pH 1 λmax 276 nm; NMR δ (DMSO-d6) 3.26 (s, 3H, CH3), 7.02 (s, 2H, NH2), 10.89 (s, 1H, NH).
Workup
- customThe reaction mixture was evaporated in vacuo
- filtrationfiltered
- washThe resulting off-white solid was washed with ethanol
- dry with materialether and dried
Sources & evidence
- ORD record
- ord-8394ae5dca82428d92de21fda8556ee3
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07098216B2
Reaction notes
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