Triethylamine → Tert-butyl 9((2-chloro-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1478027Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][N:3]=1.[NH2:10][CH:11]1[CH2:16][CH2:15][C:14]2([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:13][CH2:12]1.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][CH:11]2[CH2:12][CH2:13][C:14]3([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:18][CH2:17]3)[CH2:15][CH2:16]2)[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2,4-dichloro-5-methyl-pyrimidine (0.58 g, 3.60 mmol) and tert-butyl 3-amino-9-azaspiro[5.5]undecane-9-carboxylate (1.44 g, 5.37 mmol) in EtOH (25 mL) was added Et3N (0.86 g, 8.50 mmol). After addition, the reaction mixture was stirred at 100° C. in a sealed tube for 25.5 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2) to give the title compound as a yellow solid (332.2 mg, 24%).

Workup

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

Sources & evidence

ORD record: ord-b97d9e847eff41a0abcbec7e0d34caa7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

Loading…