HCID 71654887, compound → HCID 71654964, compound

HRID 1486529Notes

Reaction equation

HRID 1486529 reaction equation
[CH2:1]([N:8](C)[C:9]1[C:10](=[O:25])[NH:11][C:12](=[O:24])[N:13]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:16])[CH:14]=1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.[Pd]>[CH2:18]([NH:17][C:15]([N:13]1[CH:14]=[C:9]([NH:8][CH3:1])[C:10](=[O:25])[NH:11][C:12]1=[O:24])=[O:16])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 71654887HCID 71654887, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71654964HCID 71654964, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(Benzyl(methyl)amino)-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide(0.10 g, 0.28 mmol) was dissolved in EtOAc (30 mL) and hydrogenated in an H-Cube apparatus (using 10% Pd/C as catalyst, 1 bar hydrogen pressure, at 40° C.). The reaction mixture was concentrated under reduced pressure. The crude was purified by column chromatography using SI (2 g) cartridge (cyclohexane:EtOAc 85:15) to afford the title compound (0.02 g, 27%) as white powder. 1H NMR (400 MHz, DMSO-d6): δ 0.78-0.99 (m, 3H), 1.17-1.36 (m, 6H), 1.50 (dd, J=14.0, 7.0 Hz, 2H), 2.57 (s, 3H), 3.27 (dd, J=5.7, 6.9 Hz, 2H), 5.01 (s, 1H), 7.05 (s, 1H), 9.32 (t, J=5.7 Hz, 1H), 11.87 (s, 1H). 13C NMR (101 MHz, CDCl3): δ 13.85, 21.96, 25.89, 28.71, 29.70, 30.82, 40.21, 106.74, 126.49, 150.01, 150.68, 160.01. MS (ESI) m/z: 267 [M-H]−.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-b8459d37d39e4c18a72b87434406e2a0
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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