Diisopropylethylamine → tert-butyl 8-(methyl(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.5]decane-2-carboxylate

HRID 1477989Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:26])[CH:9]2[CH2:25][CH2:24][C:12]3([CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13]3)[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.Cl.[CH3:28][N:29]1[CH:33]=[C:32]([NH2:34])[CH:31]=[N:30]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:26][N:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:34][C:32]2[CH:31]=[N:30][N:29]([CH3:28])[CH:33]=2)[N:7]=1)[CH:9]1[CH2:25][CH2:24][C:12]2([CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13]2)[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of tert-butyl 8-((2-chloropyrimidin-4-yl)(methyl)amino)-2-azaspiro[4.5]decane-2-carboxylate (0.30 g, 0.79 mmol) in n-BuOH (4.0 mL) were added 1-methyl-1H-pyrazol-4-amine hydrochloride (0.21 g, 1.58 mmol) and DIPEA (0.41 g, 3.15 mmol). The mixture was stirred in a sealed tube at 150° C. overnight. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1) to give the title compound as a yellow solid (0.22 g, 63%).

Workup

concentrationThe mixture was concentrated in vacuo
customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1)

Sources & evidence

ORD record: ord-8c22f19f82b7436a8df74a5d2053af7b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

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