Sodium Cyanide → 5-Bromopyrimidine-2-carbonitrile
Reaction equation
[C-]#N.[Na+].C1N2CC[N:6](CC2)[CH2:5]1.[Br:12][C:13]1[CH:14]=[N:15][C:16](Cl)=[N:17][CH:18]=1>CS(C)=O.O>[Br:12][C:13]1[CH:14]=[N:15][C:16]([C:5]#[N:6])=[N:17][CH:18]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of NaCN (0.849 g, 17.32 mmol) and DABCO (0.390 g, 3.48 mmol) in a mixture of DMSO (4 ml) and H2O (9 ml) was added a solution of 5-bromo-2-chloropyrimidine (3.05 g, 15.75 mmol) in DMSO (9 ml). The solution was stirred at room temperature overnight, and then diluted with water, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give 5-bromopyrimidine-2-carbonitrile (2.327 g, 12.01 mmol, 76% yield, 1H NMR (CDCl3 500 MHz): δ 8.94 (s, 2H)).
Workup
- extractionextracted with EtOAc
- dry with materialThe combined organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fd48237f294746c798ba3a3ce2577919
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108938B2
Reaction notes
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