benzyl (3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazol-5-yl)carbamate → 3-[2-(dimethylamino)ethoxy]-1-methyl-1H-pyrazol-5-amine

HRID 577737

Reaction equation

HRID 577737 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([NH:11]C(=O)OCC2C=CC=CC=2)[N:8]([CH3:22])[N:7]=1>CO.[Pd]>[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([CH3:22])[N:7]=1

Participants

4

Reactant 1

HCID 86679669benzyl (3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazol-5-yl)carbamate

Product 1

HCID 866796703-[2-(dimethylamino)ethoxy]-1-methyl-1H-pyrazol-5-amineYield 79.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl (3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazol-5-yl)carbamate (1.42 g, 4.46 mmol) and 10% Pd/C (0.2 g) in MeOH (40 mL) was hydrogenated with fully inflated H2 balloon at rt overnight. The mixture was filtered and the filtrate was concentrated in vacuo to give the title compound (0.65 g, 79% yield) as a pale solid. 1H NMR (400 MHz, CDCl3) δ ppm 5.04 (s, 1H), 4.19-4.16 (t, 2H), 3.51 (s, 3H), 3.45 (bs, 2H), 2.67-2.64 (t, 2H), 2.32 (s, 6H). m/z for C8H16N4O 185.14 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e6062623629c4ccbb420a70d63da79f3
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Linked notes

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