Benzyl ((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-D]pyrimidin-2-YL)methyl)carbamate → 2-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

HRID 588711Notes

Reaction equation

HRID 588711 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([CH2:8][NH:9]C(=O)OCC2C=CC=CC=2)=[N:5][C:4]2[CH2:20][CH2:21][O:22][CH2:23][C:3]1=2>CO.[OH-].[Pd+2].[OH-]>[NH2:9][CH2:8][C:6]1[NH:7][C:2](=[O:1])[C:3]2[CH2:23][O:22][CH2:21][CH2:20][C:4]=2[N:5]=1

Participants

4

Reactant 1

HCID 135741884Benzyl ((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-D]pyrimidin-2-YL)methyl)carbamate

Product 1

HCID 1357418942-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-oneYield 75%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To benzyl (4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methylcarbamate (1.63 g, 51.7 mmol) in methanol (70 mL) was added 10% palladium hydroxide (726 mg, 0.52 mmol) and the mixture was stirred under 1 atm of H2 for 4 h. The solution was filtered through celite and concentrated under vacuum to give 2-(aminomethyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (707 mg, 75% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.34 (s, 2H) 3.83 (t, J=5.56 Hz, 2H) 3.54 (s, 2H) 2.54 (t, J=5.56 Hz, 2H).

Workup

  1. filtrationThe solution was filtered through celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3cb681cd20c74fa8b90cfc0bf6d37909
Source dataset
uspto-grants-2016_01
Patent number
US09227982B2

Reaction notes

Loading…