Formamide → HCID 178508716, compound

HRID 874385Notes

Reaction equation

HRID 874385 reaction equation
[CH:1]([NH2:3])=O.[NH2:4][C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=O)=[CH:12][CH:11]=2)[C:6]=1[C:19]#[N:20].[OH2:21]>>[N+:16]([C:13]1[CH:12]=[CH:11][C:10]([C:7]2[C:6]3[C:5](=[N:4][CH:1]=[N:3][C:19]=3[NH2:20])[NH:9][N:8]=2)=[CH:15][CH:14]=1)([O-:18])=[O:21]

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 178509386HCID 178509386, compound

Product 1

HCID 178508716HCID 178508716, compoundYield 72%

Procedure

A solution of formamide (30 mL) and 5-amino-3-(4-nitrophenyl)-1H-pyrazole-4-carbonitrile (7.25 g, 32 mmol) was heated to 160° C. overnight under an argon atmosphere. The reaction was cooled, and 25 mL of H2O was added. The resulting solid was recovered by filtration and rinsed with cold H2O to afford 3-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (5.9 g, 72% yield). ESI-MS m/z [M+H]+ found 257.5, calculated 257.2.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationThe resulting solid was recovered by filtration
  3. washrinsed with cold H2O

Sources & evidence

ORD record
ord-2af77634b82745c4aba9be8cb4144b38
Source dataset
uspto-grants-2015_03
Patent number
US08980899B2

Reaction notes

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