Acetic Acid → 2-(4,6-Dimethylpyrimidin-2-yl)octahydropyrrolo[3,4-c]pyrrole

HRID 243846Notes

Reaction equation

HRID 243846 reaction equation
CC(O)=O.C([N:12]1[CH2:19][CH:18]2[CH:14]([CH2:15][N:16]([C:20]3[N:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=3)[CH2:17]2)[CH2:13]1)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:27][C:22]1[CH:23]=[C:24]([CH3:26])[N:25]=[C:20]([N:16]2[CH2:17][CH:18]3[CH:14]([CH2:13][NH:12][CH2:19]3)[CH2:15]2)[N:21]=1

Participants

5

Reactant 2

HCID 176Acetic Acid3×HCID 671171552-Benzyl-5-(4,6-dimethyl-pyrimidin-2-yl)-octahydro-pyrrolo[3,4-c]pyrrole

Product 1

HCID 662108752-(4,6-Dimethylpyrimidin-2-yl)octahydropyrrolo[3,4-c]pyrroleYield 127.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

HOAc. To a 4 L high pressure autoclave equipped with mechanical stirring, temperature probe, heating jacket, and gas inlet were added 5% Pd/C (66.9 g, Johnson Matthey 5R338, 56.8% H2O, 3.45 mol %) and a solution of 2-benzyl-5-(4,6-dimethyl-pyrimidin-2-yl)-octahydro-pyrrolo[3,4-c]pyrrole (160 g, 519 mmol) and acetic acid (30 mL, 519 mmol) in ethanol (3.2 L). The mixture was stirred at 50° C. under 50 psi of H2(g) for 4 h. The catalyst was removed and the resulting solution was then concentrated under reduced pressure to provide the desired product as a white solid (144 g, quantitative yield) as the HOAc salt. MS (ESI): mass calcd. for C12H18N4, 218.15; m/z found 219 [M+H]+. 1H-NMR (CDCl3, 400 MHz): 6.30 (s, 1H), 3.79-3.59 (m, 4H), 3.39 (m, 2H), 3.09-2.88 (m, 4H), 2.29 (s, 6H), 1.93 (s, 3H).

Workup

  1. customTo a 4 L high pressure autoclave equipped with mechanical stirring, temperature probe
  2. temperatureheating jacket, and gas inlet
  3. customThe catalyst was removed
  4. concentrationthe resulting solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7ebe90cce1e4611922ec53f003a1b97
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

Loading…