Diisopropylethylamine → tert-butyl 5-((5-cyano-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 1478085Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)[C:5]([C:24]#[N:25])=[CH:4][N:3]=1.Cl.[CH3:27][N:28]1[CH:32]=[CH:31][C:30](N)=[N:29]1.CC[N:36](C(C)C)C(C)C>C(O)CCC>[C:24]([C:5]1[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)=[N:7][C:2]([NH:36][C:31]2[CH:30]=[N:29][N:28]([CH3:27])[CH:32]=2)=[N:3][CH:4]=1)#[N:25]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of tert-butyl 5-((2-chloro-5-cyanopyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (377.2 mg, 1.037 mmol) and 1-methylpyrazol-3-amine hydrochloride (277.5 mg, 2.077 mmol) in butan-1-ol (15 mL) was added DIPEA (335.5 mg, 2.596 mmol). The mixture was stirred at 150° C. overnight, then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1) to give the title product as a yellow solid (425 mg, 96.56%).

Workup

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

Sources & evidence

ORD record: ord-e1ebd6c13fb74b8988a0bd9faf84b98c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

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