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

HRID 1053915Notes

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)[CH:5]=[CH:4][N:3]=1.Cl.[CH3:20][N:21]1[CH:25]=[C:24]([NH2:26])[CH:23]=[N:22]1.C(N(C(C)C)C(C)C)C>CCCCO>[CH3:18][N:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:26][C:24]2[CH:23]=[N:22][N:21]([CH3:20])[CH:25]=2)[N:7]=1)[CH:9]1[CH:13]2[O:14][CH2:15][CH:16]([OH:17])[CH:12]2[O:11][CH2:10]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 6-((2-chloropyrimidin-4-yl)(methyl)amino)hexahydrofuro[3,2-b]furan-3-ol (358.0 mg, 1.32 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (178.6 mg, 1.34 mmol) in n-BuOH (5 mL) was added N-ethyldiisopropylamine (434.6 mg, 3.36 mmol). The reaction mixture was stirred at 150° C. in a sealed tube overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10) to give the title compound as a beige solid (300 mg, 68.4%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10)

Sources & evidence

ORD record: ord-f9777d53b36f41d0ae352b9ca8ca9bc4
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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