N-bromobutanimide → 6-bromo-7-(1-bromoethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
Reaction equation
[Br:1][CH:2]([C:4]1[N:5]=[C:6]2[S:13][CH:12]=[CH:11][N:7]2[C:8](=[O:10])[CH:9]=1)[CH3:3].[Br:14]N1C(=O)CCC1=O>C(#N)C>[Br:14][C:9]1[C:8](=[O:10])[N:7]2[CH:11]=[CH:12][S:13][C:6]2=[N:5][C:4]=1[CH:2]([Br:1])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 7-(1-bromo ethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (17.5 g, 67.5 mmol) and N-bromosuccinimide (14.2 g, 79.8 mmol) in acetonitrile (400 mL) was stirred at 80° C. under N2 overnight. After removal of the solvent under reduced pressure, the resulting solid was dissolved in dichloromethane, washed sequentially with water, saturated aqueous Na2S2O3 and NaHCO3 solution and brine, dried over Na2SO4, and then concentrated to give crude product (3.7 g), which was used in the next step without further purification. LCMS calculated for C8H7Br2N2OS (M+H)+: m/z=336.9. Found: 336.9.
Workup
- customAfter removal of the solvent under reduced pressure
- dissolutionthe resulting solid was dissolved in dichloromethane
- washwashed sequentially with water, saturated aqueous Na2S2O3 and NaHCO3 solution and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a7ca5a6fe12040b49c8e4c746c1c1b75
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434746B2
Reaction notes
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