Hydrochloric Acid → 1-(Methylsulfanyl-pyrimidine-4-carbonyl)hexahydro-pyridazine-3-carboxylic acid methyl ester

HRID 2415693Notes

Reaction equation

HRID 2415693 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][NH:7][NH:6]1)=[O:4].[CH3:11][S:12][C:13]1[N:18]=[C:17]([C:19](Cl)=[O:20])[CH:16]=[CH:15][N:14]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([S:12][CH3:11])[N:18]=2)=[O:20])[NH:6]1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 115429012-Methylsulfanyl-pyrimidine-4-carbonyl chlorideHCID 20596490Methyl hexahydropyridazine-3-carboxylate

Product 1

HCID 235268701-(Methylsulfanyl-pyrimidine-4-carbonyl)hexahydro-pyridazine-3-carboxylic acid methyl esterYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of hexahydro-pyridazine-3-carboxylic acid methyl ester (1.5 g, 8.3 mmol) in CH2Cl2 (80 mL) is added 2-methylsulfanyl-pyrimidine-4-carbonyl chloride, 16, (1.41 g, 7.5 mmol) and triethylamine (1.2 mL, 8.3 mmol). The mixture is stirred at room temperature for 3 hours. The reaction solution is then diluted with1 N HCl (100 mL) and the organic phase is decanted. The aqueous phase is extracted with additional solvent and the organic layers are combined, dried, and concentrated in vacuo. The crude product is purified over silica(ethyl acetate/hexane 1:1) to afford 0.9 g (36% yield) of the desired product as a yellow solid.

Workup

  1. customthe organic phase is decanted
  2. extractionThe aqueous phase is extracted with additional solvent
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified over silica(ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-dc92d9e05a3844878c54af1fabfcebb6
Source dataset
uspto-grants-2004_11
Patent number
US06821971B2

Reaction notes

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