Methylhydrazine → 1456534-36-3

HRID 717567Notes

Reaction equation

HRID 717567 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH:9]=O)=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[CH3:12][NH:13][NH2:14].C([O-])(=O)C.[Na+]>CC#N>[Cl:11][C:6]1[N:5]=[CH:4][N:3]=[C:2]2[N:13]([CH3:12])[N:14]=[CH:9][CH2:8][C:7]=12

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 517045Sodium AcetateHCID 13989292(4,6-Dichloropyrimidin-5-yl)acetaldehyde

Product 1

HCID 898160331456534-36-3Yield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (600 mg) in dry MeCN (10 mL), methyl hydrazine (154 mg) and sodium acetate (514 mg) were added. The reaction mixture was stirred at room temperature for 3 hours and solvents were removed under reduced pressure. The resulting oil was diluted with ethyl acetate (50 mL), washed with water (10 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The resulting crude product was purified by column chromatography using EtOAc/CHCl3 (0.4:9.6) as eluent to afford 5-chloro-1-methyl-1,4-dihydropyridazino[3,4-d]pyrimidine (310 mg) as white solid. 1H NMR (DMSO-d6): δ 3.34 (s, 3H), 3.53-3.54 (d, 2H), 6.91-6.93 (t, 1H), 8.38 (s, 1H).

Workup

  1. customsolvents were removed under reduced pressure
  2. additionThe resulting oil was diluted with ethyl acetate (50 mL)
  3. washwashed with water (10 mL) and brine (10 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ac1b36725a724a6aa05f1d58a5e685f2
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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