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

HRID 2036964
Notes
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Reaction equation

HRID 2036964 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 866546533-((7-Chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile

Product 1

HCID 86654654(7-(Cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylethyl)benzonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered
  3. washwashed with water
  4. customThe product, 3-((7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 83% yield
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes