HCID 15485643, compound → HCID 15485644, compound

HRID 367266Notes

Reaction equation

HRID 367266 reaction equation
[CH2:1]([N:5]1[C:10]([CH3:11])=[C:9]([N+:12]([O-])=O)[C:8](=[O:15])[N:7]([CH3:16])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]>CCOC(C)=O.[Pd]>[NH2:12][C:9]1[C:8](=[O:15])[N:7]([CH3:16])[C:6](=[O:17])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:10]=1[CH3:11]

Participants

4

Reactant 1

HCID 15485643HCID 15485643, compound

Product 1

HCID 15485644HCID 15485644, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 1.48 g (6.14 mmol) of 1-butyl-3,6-dimethyl-5-nitro-1H-pyrimidine-2,4-dione in 60 mL EtOAc was added 500 mg of 10% Pd/C. The resulting mixture was hydrogenated under 1 atm of H2 for 67 h at 23° C. The reaction mixture was then poured through Celite and the solvent evaporated to give 1.24 g (5.87 mmol, a 96% yield) of the title compound as a white solid. mp: 74-75° C.; 1H NMR (300 MHz, CDCl3): δ 0.99 (t, J=7.3 Hz, 3H), 1.40 (hex, J=7.4 Hz, 2H), 1.56-1.67 (m, 2H), 2.22 (s, 3H), 3.39 (s, 3H), 3.84 (t, J=7.3 Hz, 2H), NH2 not visible; IR (KBr, cm-1): 3142w, 2965w, 1719s, 1679s, 1627s, 1380m, 1296m, 1166s, 1063m; MS (ES) m/z (relative intensity): 363 (M+ +H, 100). Anal. Calcd for C10H17N3O2 : C, 43.03; H, 5.28; N, 15.44. Found: C, 43.11; H, 5.33; N, 15.26.

Workup

  1. additionThe reaction mixture was then poured through Celite
  2. customthe solvent evaporated
  3. customto give 1.24 g (5.87 mmol

Sources & evidence

ORD record
ord-6e3922e4ec1f4b9eaa7408f681948408
Source dataset
uspto-grants-2000_10
Patent number
US06133273

Reaction notes

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