2-(Ethoxymethylene)propanedinitrile → 7-Amino-6-cyano-2-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

HRID 54958Notes

Reaction equation

HRID 54958 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:3]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[C:20]([C:22]([C:27]#[N:28])=[CH:23]OCC)#[N:21]>C(O)(=O)C>[NH2:28][C:27]1[N:6]2[N:5]=[C:4]([C:7]3[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=3)[C:3]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:2]2[N:1]=[CH:23][C:22]=1[C:20]#[N:21]

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 178509109HCID 178509109, compound

Product 1

HCID 199572907-Amino-6-cyano-2-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidineYield 59.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-amino-3-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole (100 mg) and 1,1-dicyano-2-ethoxyethylene (49 mg) in acetic acid (2 ml) was refluxed for 1 hour. The reaction mixture was concentrated in vacuo and the residue was crystallized from ethanol to give 7-amino-6-cyano-2-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine (77 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-6b24fbafc9a143c2929c198ab30d8ffd
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

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