Ethyl Bromide → HCID 15581179, compound

HRID 223593Notes

Reaction equation

HRID 223593 reaction equation
[C:1]([C:5]1[N:10]=[N:9][C:8]2[C:11]3[CH:17]=[CH:16][C:15]([CH3:18])=[N:14][C:12]=3[S:13][C:7]=2[C:6]=1[OH:19])([O:3][CH3:4])=[O:2].[C:20](=O)(O)[O-].[K+].[CH2:25](Br)[CH3:26]>CN(C=O)C>[C:1]([C:5]1[N:10]=[N:9][C:8]2[C:11]3[CH:17]=[CH:16][C:15]([CH3:18])=[N:14][C:12]=3[S:13][C:7]=2[C:6]=1[O:19][CH2:25][CH3:26])([O:3][CH2:4][CH3:20])=[O:2]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 516893Potassium BicarbonateHCID 178499160HCID 178499160, compound

Product 1

HCID 15581179HCID 15581179, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3.3 g (0.013 mol) of 3-carbomethoxy-4-hydroxy-7-methyl-pyrido[3',2':4,5]thieno[3,2-C]pyridazine, 3.8 g potassium bicarbonate, in 90 ml of anhydrous DMF was slowly added 9 ml of ethyl bromide and stirring was continued at 60°-70° C. for 3 hours. The solvent was then removed, the residue was diluted with water and filtered to give 3.4 g of crude product. Crystallization from EtoAc-hexane gave 1.8 g (46%) of pure 3-carbethoxy-4-ethoxy-7-methyl pyrido[3',2':4,5]thieno[3,2-C]pyridazine; m.p. 158°-160° C.

Workup

  1. customThe solvent was then removed
  2. additionthe residue was diluted with water
  3. filtrationfiltered
  4. customto give 3.4 g of crude product
  5. customCrystallization from EtoAc-hexane

Sources & evidence

ORD record
ord-c71c700273384af1a1f1314b5d69b239
Source dataset
uspto-grants-1982_10
Patent number
US04355164

Reaction notes

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