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

HRID 243845Notes

Reaction equation

HRID 243845 reaction equation
C(OC([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][N:12]([C:16]3[N:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[N:17]=3)[CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:23][C:18]1[CH:19]=[C:20]([CH3:22])[N:21]=[C:16]([N:12]2[CH2:13][CH:14]3[CH:10]([CH2:9][NH:8][CH2:15]3)[CH2:11]2)[N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 671167075-(4,6-Dimethyl-pyrimidin-2-yl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester

Product 1

HCID 662108752-(4,6-Dimethylpyrimidin-2-yl)octahydropyrrolo[3,4-c]pyrroleYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4,6-Dimethyl-pyrimidin-2-yl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (0.92 g, 2.9 mmol), DCM (10 mL) and TFA (5 mL) were stirred at 23° C. for 2 h. The mixture was concentrated to remove the volatiles, diluted with EtOAc and 1N aq. NaOH, and extracted with EtOAc (3×). The organic fractions were dried and concentrated to give the title compound (0.61 g, 96%) that contained a small amount of DCM and was used as is. MS (ESI) mass calcd. for C12H18N4, 218.30; m/z found, 219.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 6.27 (s, 1H), 3.81-3.70 (m, 2H), 3.55-3.48 (m, 2H), 3.16-3.07 (m, 2H), 2.94-2.78 (m, 4H), 2.29 (s, 6H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the volatiles
  3. additiondiluted with EtOAc and 1N aq. NaOH
  4. extractionextracted with EtOAc (3×)
  5. customThe organic fractions were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-68d96cfde4a547a79d61325b82df510a
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

Loading…