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

HRID 1053928Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH:13]3[O:14][CH2:15][CH:16]([O:17][CH2:18][CH2:19][OH:20])[CH:12]3[O:11][CH2:10]2)[C:5]([Cl:21])=[CH:4][N:3]=1.Cl.[CH3:23][N:24]1[CH:28]=[C:27]([NH2:29])[CH:26]=[N:25]1.CCN(C(C)C)C(C)C>CCCCO>[Cl:21][C:5]1[C:6]([NH:8][CH:9]2[CH:13]3[O:14][CH2:15][CH:16]([O:17][CH2:18][CH2:19][OH:20])[CH:12]3[O:11][CH2:10]2)=[N:7][C:2]([NH:29][C:27]2[CH:26]=[N:25][N:24]([CH3:23])[CH:28]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 2-((6-((2,5-dichloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)oxy)ethanol (0.18 g, 0.54 mmol) in n-BuOH (5 mL) were added 1-methylpyrazol-4-amine hydrochloride (0.15 g, 1.10 mmol) and DIPEA (0.28 g, 2.18 mmol). The mixture was stirred in a sealed tube at 150° C. overnight and then concentrated in vacuo. The residue was purified by a silica chromatography (DCM/MeOH (v/v)=20/1) to give the title compound as brown sticky liquid (42 mg, 20%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by a silica chromatography (DCM/MeOH (v/v)=20/1)

Sources & evidence

ORD record: ord-ac269659b9aa4d36a78adc7bb7b8a990
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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