Methylhydrazine → HCID 89816078, compound

HRID 717575Notes

Reaction equation

HRID 717575 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9](=O)[CH3:10])=[C:6]([Cl:12])[N:5]=[CH:4][N:3]=1.[CH3:13][NH:14][NH2:15].C([O-])(=O)C.[Na+]>CC#N>[Cl:12][C:6]1[N:5]=[CH:4][N:3]=[C:2]2[N:14]([CH3:13])[N:15]=[C:9]([CH3:10])[CH2:8][C:7]=12

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 517045Sodium AcetateHCID 12927583HCID 12927583, compound

Product 1

HCID 89816078HCID 89816078, compoundYield 122%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-(4,6-dichloropyrimidin-5-yl)propan-2-one (940 mg) in dry MeCN (10 mL), methyl hydrazine (232 mg) and sodium acetate (715 mg) were added. The reaction mixture was stirred at room temperature for 24 hours before being quenched with water (100 mL). Aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic layer was washed with brine (50 mL) and dried over anhydrous Na2SO4. Evaporation of solvents under reduced pressure gave crude 5-chloro-1,3-dimethyl-1,4-dihydropyridazino[3,4-d]pyrimidine (1.1 g) as white solid which was used as was. 1H NMR (DMSO-d6): δ 2.06 (s, 3H), 3.2 (s, 3H), 3.55 (s, 2H), 8.33 (s, 1H).

Workup

  1. custombefore being quenched with water (100 mL)
  2. extractionAqueous layer was extracted with dichloromethane (2×25 mL)
  3. washThe combined organic layer was washed with brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customEvaporation of solvents under reduced pressure

Sources & evidence

ORD record
ord-3870975fa9d74be8a624d425cbd7cb3d
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

Loading…