Cyanogen Bromide → 4-(3-Bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carbonitrile

HRID 1478278Notes

Reaction equation

HRID 1478278 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][C:6]=12.C(=O)(O)[O-].[Na+].[N:22]#[C:23]Br>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:23]#[N:22])[CH2:13][CH2:12]3)=[N:7][C:6]=12

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 866974343-Bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 866974444-(3-Bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine (500 mg, 1.77 mmol) taken up in 20 mL DCM and stirred at 0° C. in an ice bath. Sodium bicarbonate (744 mg, 8.86 mmol) in 6 mL water added and stirred. Cyanogen bromide (225 mg, 2.12 mmol) added and stirred at 0° C. for 30 minutes then allowed to reach room temperature and stirred overnight. Reaction diluted with DCM washed with water, DCM layer dried over magnesium sulfate reduced in vacuo for 500 mg crude product for further reaction as is. LRMS (ESI) m/z 307/309 [(M+H)]+, calc'd for C11H11BrN6: 307.15.

Workup

  1. stirringstirred
  2. stirringstirred at 0° C. for 30 minutes
  3. customto reach room temperature
  4. stirringstirred overnight
  5. customReaction
  6. washwashed with water, DCM layer
  7. dry with materialdried over magnesium sulfate
  8. customreduced in vacuo for 500 mg crude product for further reaction

Sources & evidence

ORD record
ord-71a8c1e670ec46c58069136eb98079c4
Source dataset
uspto-grants-2016_08
Patent number
US09403832B2

Reaction notes

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