Triethylamine → 5,6-Dimethyl-4,5,6,7-tetrahydrothiazolo[4,5-d]pyridazine

HRID 352888Notes

Reaction equation

HRID 352888 reaction equation
Br[CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1[CH2:8]Br.Cl.Cl.[CH3:12][NH:13][NH:14][CH3:15].C(N(CC)CC)C>C(O)C>[CH3:12][N:13]1[CH2:2][C:3]2[N:4]=[CH:5][S:6][C:7]=2[CH2:8][N:14]1[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 108496984,5-Bis(bromomethyl)thiazole

Product 1

HCID 184427415,6-Dimethyl-4,5,6,7-tetrahydrothiazolo[4,5-d]pyridazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under ice cooling, 4,5-bis(bromomethyl)thiazole (600 mg) and 1,2-dimethylhydrazine dihydrochloride (294 mg) were suspended in ethanol (20 ml). Triethylamine (1.23 ml) was added in one portion to the reaction mixture, followed by stirring at room temperature for 30 minutes and then, at 50° C. for 30 minutes. The solvent was distilled off and the residue was purified by chromatography on a silica gel column (5% methanol—methylene chloride), whereby the title compound (90 mg, 24%) was obtained.

Workup

  1. waitat 50° C. for 30 minutes
  2. distillationThe solvent was distilled off
  3. customthe residue was purified by chromatography on a silica gel column (5% methanol—methylene chloride), whereby the title compound (90 mg, 24%)
  4. customwas obtained

Sources & evidence

ORD record
ord-d27dc1db52c34ccfb27bdf9f7684590e
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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