Triethylamine → HCID 18921357, compound

HRID 1289374Notes

Reaction equation

HRID 1289374 reaction equation
[N:1]([C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH:5](O)[C:6]([O:8][CH3:9])=[O:7])=[N+:2]=[N-:3].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[N:35]=[C:34]([SH:40])[N:33]=1.C(=O)([O-])O.[Na+]>ClCCl.CN(C=O)C>[N:1]([C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH:5]([S:40][C:34]1[N:33]=[C:32]([O:31][CH3:30])[CH:37]=[C:36]([O:38][CH3:39])[N:35]=1)[C:6]([O:8][CH3:9])=[O:7])=[N+:2]=[N-:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 15789718HCID 15789718, compoundHCID 178493561HCID 178493561, compound

Product 1

HCID 18921357HCID 18921357, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5.9 g (25 mmol) of methyl 3-azido-3-phenyl-2-hydroxybutyrate (Ex. 1) are dissolved in 50 ml of dichloromethane, 3 g (30 mmol) of triethylamine are added and 3.2 g (28 mmol) of methanesulfonyl chloride are added dropwise with stirring. The mixture is stirred for 23 hours at room temperature, washed three times with 100 ml of water each time, dried over sodium sulfate and concentrated under reduced pressure. The residue is taken up in 100 ml of DMF and added dropwise at 0° C. to a suspension of 12.9 g (75 mmol) of 4,6-dimethoxypyrimidine-2-thiol and 8.4 g (100 mmol) of sodium hydrogencarbonate in 100 ml of DMF. After stirring at room temperature for 2 hours and at 60° C. for a further 2 hours, the mixture is poured onto 1 l of ice water and the resulting precipitate is filtered off with suction.

Workup

  1. stirringThe mixture is stirred for 23 hours at room temperature
  2. washwashed three times with 100 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. stirringAfter stirring at room temperature for 2 hours and at 60° C. for a further 2 hours
  6. filtrationthe resulting precipitate is filtered off with suction

Sources & evidence

ORD record
ord-9a06e2dd0ca04445833c8a751228ae2c
Source dataset
uspto-grants-1998_05
Patent number
US05750469

Reaction notes

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