Acetonitrile → (7-(Cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylethyl)benzonitrile

HRID 2036964Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To the reaction flask, 3((7-chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile (400 mg, 1.5 mmol) was added along with cyclopropylamine (115 μL, 1.6 mmol), triethylamine (230 μL, 1.6 mmol), and acetonitrile (3 mL). The reaction was stirred at room temperature for 8 hours at 80° C. then cooled to room temperature, diluted with water, filtered and washed with water. The product, 3-((7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 83% yield after drying under vacuum overnight. LCMS (M+1=290)

Workup

temperaturethen cooled to room temperature
filtrationfiltered
washwashed with water
customThe product, 3-((7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 83% yield
customafter drying under vacuum overnight

Sources & evidence

ORD record: ord-b944f62468f14de5b3e88cba04317cd4
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575177B2

Reaction notes

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