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

HRID 1053922Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][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.[CH3:18][N:19]1[CH:23]=[C:22]([NH2:24])[CH:21]=[N:20]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:18][N:19]1[CH:23]=[C:22]([NH:24][C:2]2[N:7]=[C:6]([NH:8][CH:9]3[CH:13]4[O:14][CH2:15][CH:16]([OH:17])[CH:12]4[O:11][CH2:10]3)[CH:5]=[CH:4][N:3]=2)[CH:21]=[N:20]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 6-((2-chloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-ol (354 mg, 1.37 mmol) in n-BuOH (3 mL) were added 1-methyl-1H-pyrazol-4-amine (220 mg, 1.65 mmol) and DIPEA (531 mg, 4.11 mmol). Then the mixture was stirred under nitrogen atmosphere at 150° C. overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1) to give the title compound as a yellow solid (120 mg, 22%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1)

Sources & evidence

ORD record: ord-b387fcd5fdd241abbd2cbb1f1ff13196
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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