Hydrazine → HCID 178492932, compound

HRID 238009Notes

Reaction equation

HRID 238009 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10](OC)=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[NH2:18][NH2:19]>CCO>[NH2:13][C:12]1[NH:19][N:18]=[C:10]([C:4]2[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([F:1])[CH:3]=2)[C:11]=1[C:14]#[N:15]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 866170152-((3-Fluoro-5-methoxyphenyl)(methoxy)methylene)malononitrile

Product 1

HCID 178492932HCID 178492932, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-((3-fluoro-5-methoxyphenyl)(methoxy)methylene)malononitrile (BA69, 0.029 mol) stirred in EtOH (20 ml) at room temperature under an argon atmosphere. Hydrazine (1.4 ml, 29 mmol) was added and reaction was left stirring for 90 minutes. Reaction mixture was concentrated in vacuo and dried on vacuum pump overnight to yield intermediate 5-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazole-4-carbonitrile (BA73). Formamide (20 ml) was added and reaction was heated to 180° C. under an argon atmosphere overnight. Reaction was cooled and dH2O was added (40 ml) forcing a white precipitate out of solution. Precipitate was collected and washed with dH2O. Solid was dried and purified by silica gel column chromatography [MeOH—CH2Cl2, 10:90] to yield 3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA75).

Workup

  1. customreaction
  2. waitwas left
  3. customReaction mixture
  4. concentrationwas concentrated in vacuo
  5. customdried on vacuum pump overnight

Sources & evidence

ORD record
ord-40a0ddffab1b4b7788a4b576db8df227
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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