Methanol → 6-Isopropoxypyrimidine-2,4-diamine
Reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([OH:10])[CH:7]=[C:6]([NH2:11])[N:5]=1.[CH:12](Br)([CH3:14])[CH3:13].CO>CN(C=O)C>[CH:12]([O:10][C:8]1[N:9]=[C:4]([NH2:3])[N:5]=[C:6]([NH2:11])[CH:7]=1)([CH3:14])[CH3:13]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
634 mg of sodium hydride (60% in mineral oil, 17.12 mmol) are added in portions under an argon atmosphere to a vigorously stirred solution of 1.8 g (14.27 mmol) of 2,6-diaminopyrimidin-4-ol in 20 ml of DMF. After 30 min, 1.6 ml (17.12 mmol) of isopropyl bromide are added dropwise, and the solution is stirred at 40° C. for 12 h. Methanol (1 mol) is then added to the reaction mixture, which is directly purified by preparative HPLC. Combining the product fractions and removing the solvent result in 250 mg (12% of theory) of the title compound as a white solid.
Workup
- customis directly purified by preparative HPLC
- customremoving the solvent
Sources & evidence
- ORD record
- ord-db5fb98a943a402caf8c7c4af9d3b453
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399471B2
Reaction notes
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