Tert-butyl ((5-cyano-6-methoxy-4-methylpyridin-2-yl)methyl)carbamate → Tert-butyl ((5-(aminomethyl)-6-methoxy-4-methylpyridin-2-yl)methyl)carbamate
Reaction equation
[C:1]([C:3]1[C:4]([CH3:20])=[CH:5][C:6]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N:7][C:8]=1[O:9][CH3:10])#[N:2]>CC(O)=O.C(O)C.[Ni]>[NH2:2][CH2:1][C:3]1[C:4]([CH3:20])=[CH:5][C:6]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[N:7][C:8]=1[O:9][CH3:10]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A clear solution of tert-butyl ((5-cyano-6-methoxy-4-methylpyridin-2-yl)methyl)carbamate (0.65 g, 2.344 mmol) in HOAc (5 mL) and Ethanol (20 mL) was treated on an H-Cube apparatus (50 psi, 40° C., 1 mL/min., Raney Nickel cartridge) for 18 hr overnight. LCMS showed that the reaction was complete. The reaction was evaporated to dryness under vacuum. Purified by silica gel chromatography (Analogix, SF25-60 g, 0 to 10% (5% NH4OH/MeOH) in CH2Cl2). The pure fractions were combined and evaporated to dryness under vacuum to give the product tert-butyl ((5-(aminomethyl)-6-methoxy-4-methylpyridin-2-yl)methyl)carbamate (0.58 g, 2.061 mmol, 88% yield) as a clear thick oil. 1H NMR (400 MHz, DMSO-d6) δ 7.31 (t, J=6.1 Hz, 1H), 6.63 (s, 1H), 4.06 (d, J=6.3 Hz, 2H), 3.84 (s, 3H), 3.61 (s, 2H), 2.29 (s, 3H), 1.53 (br. s., 2H), 1.41 (s, 9H). MS(ES)+ m/e 282.2 [M+H]+.
Workup
- customThe reaction was evaporated to dryness under vacuum
- customPurified by silica gel chromatography (Analogix
- customevaporated to dryness under vacuum
Sources & evidence
- ORD record
- ord-1d4ea630b5c24dec82ddafb9ebbaac56
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09114141B2
Reaction notes
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