Diisopropylethylamine → HCID 118387978, compound

HRID 1053920Notes

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)[C:5]([CH3:18])=[CH:4][N:3]=1.[CH3:19][N:20]1[CH:24]=[C:23]([NH2:25])[CH:22]=[N:21]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:18][C:5]1[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)=[N:7][C:2]([NH:25][C:23]2[CH:22]=[N:21][N:20]([CH3:19])[CH:24]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 6-((2-chloro-5-methylpyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-ol (54 mg, 0.20 mmol) in n-BuOH (1 mL) was added 1-methyl-1H-pyrazol-4-amine (32 mg, 0.24 mmol) and DIPEA (78 mg, 0.60 mmol). Then the mixture was stirred under nitrogen atmosphere at 150° C. overnight and concentrated in vacuo. To the residue was added water (20 mL), and extracted with DCM (20 mL×3). The combined organic phases were washed with brine (30 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give crude oil. Then it was purified by silica gel column chromatography (DCM/MeOH (v/v)=20/1) to give the title compound as an off-white solid (46 mg, 70%).

Workup

concentrationconcentrated in vacuo
additionTo the residue was added water (20 mL)
extractionextracted with DCM (20 mL×3)
washThe combined organic phases were washed with brine (30 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give crude oil
customThen it was purified by silica gel column chromatography (DCM/MeOH (v/v)=20/1)

Sources & evidence

ORD record: ord-5158fbd8633747c0adbe4f16f5d3a4e2
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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