Triethylamine → Tert-butyl 8-((2-chloropyrimidin-4-yl)(methyl)amino)-2-azaspiro[4.5]decane-2-carboxylate

HRID 1056625Notes

Reaction equation

HRID 1056625 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][NH:10][CH:11]1[CH2:27][CH2:26][C:14]2([CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16][CH2:15]2)[CH2:13][CH2:12]1.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([N:10]([CH3:9])[CH:11]2[CH2:27][CH2:26][C:14]3([CH2:18][N:17]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:16][CH2:15]3)[CH2:13][CH2:12]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 118390014Tert-butyl 8-(methylamino)-2-azaspiro[4.5]decane-2-carboxylate

Product 1

HCID 118390055Tert-butyl 8-((2-chloropyrimidin-4-yl)(methyl)amino)-2-azaspiro[4.5]decane-2-carboxylateYield 38.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloropyrimidine (596 mg, 4.0 mmol) and tert-butyl 8-(methylamino)-2-azaspiro[4.5]decane-2-carboxylate (1.29 g, 4.8 mmol) in EtOH (10 mL) was added Et3N (0.92 g, 9.1 mmol) and the reaction mixture was stirred at rt overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2) to give the product as a pale yellow solid (580 mg, 38.1%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2)

Sources & evidence

ORD record
ord-1d78c04ad92d4f9f8c0cd8ff171cad68
Source dataset
uspto-grants-2016_07
Patent number
US09399637B2

Reaction notes

Loading…