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

HRID 1053914Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 6-((2,5-dichloropyrimidin-4-yl)(methyl)amino)hexahydrofuro[3,2-b]furan-3-ol (342.2 mg, 1.12 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (185.0 mg, 1.38 mmol) in n-BuOH (5 mL) was added N-ethyldiisopropylamine (358.8 mg, 2.78 mmol). The reaction mixture was stirred at 150° C. in a sealed tube overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/40) to give the title compound as a beige solid (156 mg, 38.0%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/40)

Sources & evidence

ORD record: ord-963bf465951a4912a34b1e793166e81f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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