Diisopropylethylamine → 2-(6-((5-chloro-2-((l-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

HRID 1053943Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH:13]3[O:14][CH2:15][CH:16]([N:17]4[C:25](=[O:26])[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:18]4=[O:27])[CH:12]3[O:11][CH2:10]2)[C:5]([Cl:28])=[CH:4][N:3]=1.Cl.[CH3:30][N:31]1[CH:35]=[C:34]([NH2:36])[CH:33]=[N:32]1.CCN(C(C)C)C(C)C>CCCCO>[Cl:28][C:5]1[C:6]([NH:8][CH:9]2[CH:13]3[O:14][CH2:15][CH:16]([N:17]4[C:25](=[O:26])[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:18]4=[O:27])[CH:12]3[O:11][CH2:10]2)=[N:7][C:2]([NH:36][C:34]2[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 2-(6-((2,5-dichloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl) isoindoline-1,3-dione (370.0 mg, 0.88 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (354.2 mg, 2.65 mmol) in n-BuOH (10 mL) was added DIPEA (683.1 mg, 5.29 mmol). The mixture was stirred at 150° C. overnight. The mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (MeOH/CH2C12 (v/v)=1/30) to give the title compound as a red solid (140.0 mg, 33.1%).

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue was purified by silica gel column chromatography (MeOH/CH2C12 (v/v)=1/30)

Sources & evidence

ORD record: ord-011255ade86445b29bd87cb8aa169f85
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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