Triethylamine → tert-butyl 5-((2-chloro-5-cyanopyrimidin-4-yl)amino)hexahvdrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 1478084Notes

Reaction equation

HRID 1478084 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[CH:4][N:3]=1.[NH2:11][CH:12]1[CH2:26][CH:15]2[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH:14]2[CH2:13]1.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:11][CH:12]2[CH2:26][CH:15]3[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:18][CH:14]3[CH2:13]2)[C:5]([C:9]#[N:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 140269072,4-Dichloro-5-cyanopyrimidineHCID 59011518Tert-butyl 5-amino-octahydrocyclopenta[c]pyrrole-2-carboxylate

Product 1

HCID 118390007tert-butyl 5-((2-chloro-5-cyanopyrimidin-4-yl)amino)hexahvdrocyclopenta[c]pyrrole-2(1H)-carboxylateYield 26.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloropyrimidine-5-carbonitrile (600 mg, 3.4485 mmol) and tert-butyl 5-aminohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (936.8 mg, 4.139 mmol) in ethanol (50 mL) was added N,N-diethylethanamine (698.5 mg, 6.903 mmol). The mixture was stirred at rt for 3 h. Then it was concentrated under vacuo, and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=5/1) to give the title product as yellow oil (332.5 mg, 26.50%).

Workup

  1. concentrationThen it was concentrated under vacuo
  2. customthe residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=5/1)

Sources & evidence

ORD record
ord-0f5d7aa9dba04c0f85f6000e4dc665bd
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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