Diisopropylethylamine → tert-butyl 4-(methyl(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.4]nonane-2-carboxylate

HRID 1477948Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:25])[CH:9]2[C:13]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:4][N:3]=1.Cl.[CH3:27][N:28]1[CH:32]=[C:31]([NH2:33])[CH:30]=[N:29]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:25][N:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:33][C:31]2[CH:30]=[N:29][N:28]([CH3:27])[CH:32]=2)[N:7]=1)[CH:9]1[C:13]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of tert-butyl 4-((2-chloropyrimidin-4-yl)(methyl)amino)-2-azaspiro[4.4]nonane-2-carboxylate (0.34 g, 0.93 mmol) in n-BuOH (5.0 mL) was added 1-methyl-1H-pyrazol-4-amine hydrochloride (0.25 g, 1.85 mmol) and DIPEA (0.48 g, 3.71 mmol). The mixture was stirred in a sealed tube and heated to 150° C. overnight, then concentrated in vacuo. The residue was purified by silica gel column chromatography (EA) to give the product as a yellow solid (0.22 g, 55%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EA)

Sources & evidence

ORD record: ord-d1dd1f1e34f24995a05388cab058c83f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

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