Ammonia → 2-(Methylthio)pyrimidin-4-amine
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[NH3:10]>CO>[CH3:9][S:8][C:4]1[N:3]=[C:2]([NH2:10])[CH:7]=[CH:6][N:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-chloro-2-methylsulfanylpyrimidine (8 g) and 7N ammonia in methanol (100 mL) at 100° C. was stirred for 2 days in a sealed tube, cooled, concentrated, treated with water, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The concentrate was triturated with ethyl ether and filtered. 1H NMR (300 MHz, CDCl3) δ 8.06 (d, 1H), 6.12 (d, 1H), 4.83 (s, 2H), 2.51 (s, 3H).
Workup
- temperaturecooled
- concentrationconcentrated
- additiontreated with water
- extractionextracted with ethyl acetate
- washThe extract was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe concentrate was triturated with ethyl ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-ee4c67b25ee64efdb3c0893c80b0defa
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737159B2
Reaction notes
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