Methylhydrazine → HCID 86724094, compound

HRID 1748752

Reaction equation

HRID 1748752 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)=[N:3]1.COC(C1C=CN=CN=1)=O.[H-].[Na+].CNN.[Br:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[C:32]([CH3:38])[CH:31]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[Br:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[C:5]2[C:6](=[NH:7])[N:2]([CH3:1])[N:3]=[C:4]2[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)=[C:32]([CH3:38])[CH:31]=1

Participants

8

Reactant 6

HCID 6061MethylhydrazineHCID 6101p-Toluenesulfonic acidHCID 24758Sodium hydrideHCID 254248Methyl pyrimidine-4-carboxylateHCID 135551504-Bromo-2-methylbenzaldehydeHCID 86724095HCID 86724095, compound

Product 1

HCID 86724094HCID 86724094, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To the suspension of 1-methyl-3-(pyrimidin-4-yl)-1H-pyrazol-5-amine (0.42 g, 2.4 mmol, prepared using A with methylpyrimidine-4-carboxylate (Ark Pharm) with NaH followed by B with methyl hydrazine) and 4-bromo-2-methylbenzaldehyde (0.48 g, 2.40 mmol, Ark Pharm) in acetonitrile (15 mL) was added p-TSA (0.09 g, 0.5 mmol) and heated to about 50° C. for about 5 h. The reaction mixture was cooled to ambient temperature and continued to stir for about 16 h. The precipitate was collected by filtration and dried under reduced pressure to afford 4-(4-bromo-2-methylbenzylidene)-1-methyl-3-(pyrimidin-4-yl)-1H-pyrazol-5(4H)-imine (0.43 g, 51%) as a light brown solid. LC-MS MS (Table 1, Method g) Rt=2.48 min, m/z 356, 358 (M+H)+.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. filtrationThe precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-cc7b99e24e194ba2bab0c8920f565776
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Linked notes

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