Lithium borohydride → (6-Aminopyrimidin-4-yl)methanol
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](OC)=[O:9])[CH:3]=1.[Li+].[BH4-]>CO>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a stirred solution of methyl 6-aminopyrimidine-4-carboxylate (2.0 g, 13 mmol) in MeOH (20 mL) at 25° C., was added LiBH4 (0.85 g, 39 mmol). After addition, the resulting mixture was allowed to stir at 70° C. for 16 hours. TLC indicated the starting material was consumed completely at this point. Solvents were removed under reduced pressure and the residue was purified via chromatography column on silica gel eluting with a 5% gradient of methanol in dichloromethane to give the desired alcohol as pale yellow oil (1.0 g, 61% yield). LCMS (ESI) m/z: 126.1 [M+H+].
Workup
- additionAfter addition
- customwas consumed completely at this point
- customSolvents were removed under reduced pressure
- customthe residue was purified via chromatography column on silica gel eluting with a 5% gradient of methanol in dichloromethane
Sources & evidence
- ORD record
- ord-4844b7b696b44e889a7cf08ae9bb0d30
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697708B2
Reaction notes
Loading…