Triethylamine → HCID 118390023, compound

HRID 1478018Notes

Reaction equation

HRID 1478018 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][N:3]=1.[CH3:10][NH:11][CH:12]1[CH2:29][CH2:28][C:15]2([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:14][CH2:13]1.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:11]([CH3:10])[CH:12]2[CH2:29][CH2:28][C:15]3([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17][CH2:16]3)[CH2:14][CH2:13]2)[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 118390114HCID 118390114, compound

Product 1

HCID 118390023HCID 118390023, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,4-dichloro-5-methylpyrimidine (300 mg, 1.84 mmol) and tert-butyl 9-(methylamino)-3-azaspiro[5.5]undecane-3-carboxylate (573.32 mg, 2.03 mmol) in ethanol (30 mL) was added N,N-diethylethanamine (372.38 mg, 3.68 mmol). The reaction mixture was stirred at 100° C. overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5) to give the title compound as yellow oil (165 mg, 22%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5)

Sources & evidence

ORD record
ord-78b85dda3766451e975682596be5a23e
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

Loading…