HCID 12988759, compound → HCID 12988760, compound

HRID 1744239Notes

Reaction equation

HRID 1744239 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([N+:14]([O-])=O)[C:11](=[O:17])[N:10]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[NH2:14][C:12]1[C:11](=[O:17])[N:10]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:9](=[O:23])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 12988759HCID 12988759, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12988760HCID 12988760, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

EX-1B) A solution of 1-Benzyl-3-methoxycarbonylmethyl-5-nitro-2,4(1H,3H) pyrimidinedione (EX-1A; 6.30 g, 19.74 mmol) in 100.0 mL methanol was degassed with hydrogen gas. The solution was then added 5% Pd/C (0.737 g) and allowed to stir under an atmosphere of hydrogen at room temperature for 24 hours. The crude reaction was filtered through a pad of Celite 545 and concentrated under reduced pressure. The oil was purified by MPLC (60% Ethyl acetate/hexanes) to give pure 5-amino-1-Benzyl-3-methoxycarbonylmethyl-2,4(1H,3H)-pyrimidinedione (EX-1B) in 63% yield as a tan solid: 1H NMR (300 MHz, DMSO) δ 7.41–7.28 (m, 5H), 6.93 (s, 1H), 4.93 (s, 2H), 4.66 (s, 2H), 4.32 (s, 2H), 3.69 (s, 3H); HRMS (ES) calcd for C14H16N3O4 290.1141, found 290.1138.

Workup

  1. customThe crude reaction
  2. filtrationwas filtered through a pad of Celite 545
  3. concentrationconcentrated under reduced pressure
  4. customThe oil was purified by MPLC (60% Ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0b04fe0f174442a998dd61a6abfe3d16
Source dataset
uspto-grants-2006_03
Patent number
US07015230B1

Reaction notes

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