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 588710Notes

Reaction equation

HRID 588710 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.[Pd]>[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 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl (4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methylcarbamate (55.5 g, 176 mmol) in methanol (4 L) was degassed several times under nitrogen then palladium on carbon (1.87 g, 1.76 mmol, 10% on carbon) was added slowly under nitrogen atmosphere. The mixture was stirred under a hydrogen balloon at ambient temperature until TLC showed complete consumption of starting material. Filtration through a pad of Celite and evaporation of solvent provided the title compound (32 g, >99% yield). 1H NMR (400 MHz, CD3OD) δ 4.49 (s, 2H), 3.93 (t, J=5.5 Hz, 2H), 3.77 (s, 2H), 2.66 (t, J=5.5 Hz, 2H). MS m/z 182.2 (M+1), retention time=0.39 min.

Workup

  1. customconsumption of starting material
  2. filtrationFiltration
  3. customthrough a pad of Celite and evaporation of solvent

Sources & evidence

ORD record
ord-b01cb63cc7d34380a12d9d0ee94f388b
Source dataset
uspto-grants-2016_01
Patent number
US09227982B2

Reaction notes

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