Pyridine → 5-bromo-N-tert-butylpyrimidine-2-carboxamide
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24]>ClCCl.CN(C=O)C>[C:23]([NH:27][C:8]([C:5]1[N:6]=[CH:7][C:2]([Br:1])=[CH:3][N:4]=1)=[O:10])([CH3:26])([CH3:25])[CH3:24]Participants
Conditions
- Temperature
- 2.5 °C
Procedure
5-Bromopyrimidine-2-carboxylic acid (1 g, 4.93 mmol) was suspended in dichloromethane (10 ml) and DMF (20 μl). Oxalyl chloride (520 μl, 5.91 mmol, 1.2 equiv.) was added drop wise at room temperature and the mixture was stirred for 16 hours. The reaction mixture was then cooled to 0-5° C. and pyridine (480 μl, 5.91 mmol, 1.2 equiv.) and tert-butyl amine (621 μl, 5.91 mmol, 1.2 equiv.) were added drop wise at 0-5° C. The mixture was stirred for 4 hours at room temperature. The reaction mixture was extracted with saturated NaHCO3 solution and dichloromethane. The organic layers were extracted with water and brine, dried over sodium sulfate and evaporated to dryness. The desired 5-bromo-pyrimidine-2-carboxylic acid tert-butylamide (960 mg, 76% yield) was obtained as a light yellow solid, MS: m/e=258.0/259.9 (M+H+).
Workup
- stirringThe mixture was stirred for 4 hours at room temperature
- extractionThe reaction mixture was extracted with saturated NaHCO3 solution and dichloromethane
- extractionThe organic layers were extracted with water and brine
- dry with materialdried over sodium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-84ae8905ddeb42e0b74f227e4368745f
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772300B2
Reaction notes
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