Methylhydrazine → 1-Methyl-5-(pyridin-2-yl)-1,4-dihydropyrimido[4,5-c]pyridazine

HRID 717572Notes

Reaction equation

HRID 717572 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH:9]=O)=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:5]=[CH:4][N:3]=1.[CH3:17][NH:18][NH2:19].C([O-])(=O)C.[Na+]>CC#N>[CH3:17][N:18]1[C:2]2[N:3]=[CH:4][N:5]=[C:6]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:7]=2[CH2:8][CH:9]=[N:19]1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 517045Sodium AcetateHCID 898152122-(4-Chloro-6-(pyridin-2-yl)pyrimidin-5-yl)acetaldehyde

Product 1

HCID 898158061-Methyl-5-(pyridin-2-yl)-1,4-dihydropyrimido[4,5-c]pyridazineYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-(4-chloro-6-(pyridin-2-yl)pyrimidin-5-yl)acetaldehyde (600 mg) in dry MeCN (10 mL), methyl hydrazine (181 mg) and sodium acetate (422 mg) were added. The reaction mixture was stirred at room temperature for 3 hours and solvents were removed under reduced pressure. The resulting crude was purified by column chromatography using MeOH/CHCl3 (0.5:9.5) as eluent to afford 1-methyl-5-(pyridin-2-yl)-1,4-dihydropyrimido[4,5-c]pyridazine (350 mg) as white solid. 1H NMR (DMSO-d6): δ 3.41 (s, 3H), 3.93-3.94 (d, 2H), 6.92-6.94 (t, 1H), 7.47-7.51 (m, 1H), 7.94-7.99 (m, 1H), 8.00-8.10 (m, 1H), 8.67-8.69 (d, 2H).

Workup

  1. customsolvents were removed under reduced pressure
  2. customThe resulting crude was purified by column chromatography

Sources & evidence

ORD record
ord-ac7f2ee0a0be415eb8e1c295575fa830
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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