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Acetonitrile → 3-(3-methyl-4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1853033
Notes
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Reaction equation

HRID 1853033 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[C:14]([CH3:18])=[N:15][NH:16][CH:17]=3)[N:10]3[CH:19]=[CH:20][N:21]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1.[C:22](#[N:25])[CH:23]=[CH2:24].C(#N)C.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH3:18][C:14]1[C:13]([C:11]2[N:10]3[CH:19]=[CH:20][N:21]=[C:9]3[CH:8]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[N:12]=2)=[CH:17][N:16]([CH2:24][CH2:23][C:22]#[N:25])[N:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7855AcrylonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178434538HCID 178434538, compound

Product 1

HCID 682321613-(3-methyl-4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrileYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with 7-(1-methyl-1H-pyrazol-4-yl)-5-(3-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (0.025 g, 0.090 mmol) and acrylonitrile (0.032 mL, 0.49 mmol) was added 1 mL of acetonitrile and DBU (0.027 mL, 0.18 mmol) and the flask was sealed under nitrogen and allowed to proceed at ambient temperature overnight. The reaction was diluted with 3 mL of DCM, loaded directly onto a silica gel column and eluted with 1% MeOH in EtOAc containing 1% NH4OH to afford a mixture of regioisomers from alkylation at N-1 and N-2. The mixture was purified by silica gel chromatography, eluting with a gradient of 1.0-5.0% MeOH in DCM with 0.5% NH4OH to afford the title compound (5.0 mg, 0.0150 mmol, 17% yield). MS (apci) m/z=333.1 (M+H). The structure and regioisomer were confirmed by observed nOe signals.

Workup

  1. customthe flask was sealed under nitrogen
  2. washeluted with 1% MeOH in EtOAc containing 1% NH4OH
  3. customto afford
  4. additiona mixture of regioisomers from alkylation at N-1 and N-2
  5. customThe mixture was purified by silica gel chromatography
  6. washeluting with a gradient of 1.0-5.0% MeOH in DCM with 0.5% NH4OH

Sources & evidence

ORD record
ord-a83fa16c217a4df2b475c15c5648a90c
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962596B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes