Diisopropylethylamine → Methyl 2-(5-bromopyrimidin-2-yl)octahydrocyclopenta[c]pyrrole-3a-carboxylate

HRID 712226Notes

Reaction equation

HRID 712226 reaction equation
[CH2:1]1[CH:5]2[CH2:6][CH2:7][CH2:8][C:4]2([C:9]([O:11][CH3:12])=[O:10])[CH2:3][NH:2]1.CCN(C(C)C)C(C)C.[Br:22][C:23]1[CH:24]=[N:25][C:26](Cl)=[N:27][CH:28]=1>CCO>[Br:22][C:23]1[CH:24]=[N:25][C:26]([N:2]2[CH2:3][C:4]3([C:9]([O:11][CH3:12])=[O:10])[CH2:8][CH2:7][CH2:6][CH:5]3[CH2:1]2)=[N:27][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 66977181Methyl octahydrocyclopenta[c]pyrrole-3a-carboxylate

Product 1

HCID 66977056Methyl 2-(5-bromopyrimidin-2-yl)octahydrocyclopenta[c]pyrrole-3a-carboxylateYield 45.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of methyl octahydrocyclopenta[c]pyrrole-3a-carboxylate (1.0 g, 5.91 mmol) in EtOH (10.0 mL) was added DIPEA (2.80 mL, 16.12 mmol) at rt and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (1.10 g, 5.37 mmol). The reaction was heated up to 70° C. for 2 h. After completion (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 7.0% EtOAc:hexane to obtain the desired product as a white solid (0.80 g, 45%). MS: 326.19 [M+H]+.

Workup

  1. temperatureThe reaction was heated up to 70° C. for 2 h
  2. customAfter completion (by TLC), solvent was evaporated
  3. customthe crude residue purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-1ae1ed5c783d476ca67b70c8bdde70ec
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…