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

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-methyl-1H-pyrazol-4-amine	HCID 4770990	—
Reactant	6((2-Chloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-ol	HCID 118387969	—
Solvent	1-Butanol	HCID 263	—
Product	6-((2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-ol	HCID 118387951	27.5%

Reaction Conditions

Temperature	150 °C

Reaction Steps

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%).

Provenance & Evidence

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