Nitrogen → Pyrazolo[1,5-a]pyriMidine-5-carbonitrile

HRID 1890571Notes

Reaction equation

HRID 1890571 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][CH:10]=[C:4]2[N:3]=1.N#N.[CH3:13][N:14](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:8]1[N:5]2[CH:6]=[CH:7][C:2]([C:13]#[N:14])=[N:3][C:4]2=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 6228DimethylformamideHCID 210717595-Chloropyrazolo(1,5-a)pyrimidine

Product 1

HCID 23156341Pyrazolo[1,5-a]pyriMidine-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

To a mixture of 5-chloropyrazolo[1,5-a]pyrimidine (2-1) (1.0 g, 6.45 mmol) and Zn(CN)2 (770 mg, 6.58 mmol) in dried DMF (20 mL) exchanged by N2 was added Pd(PPh3)4 (400 mg, 3.46 mmol). The reaction mixture was stirred at 110° C. overnight. After cooled to the room temperature, the solution was concentrated and purified by chromatography on silica gel to afford the title compound (620 mg)

Workup

  1. temperatureAfter cooled to the room temperature
  2. concentrationthe solution was concentrated
  3. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-9a7b5b65375e4e569f5106a99c593a5b
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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