Triethylamine → HCID 18916377, compound

HRID 1290618Notes

Reaction equation

HRID 1290618 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([F:14])([CH3:13])[CH:7](O)[C:8]([O:10][CH3:11])=[O:9].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:27][O:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[N:32]=[C:31]([SH:37])[N:30]=1.C(=O)([O-])O.[Na+]>ClCCl.CN(C)C=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([F:14])([CH3:13])[CH:7]([S:37][C:31]1[N:30]=[C:29]([O:28][CH3:27])[CH:34]=[C:33]([O:35][CH3:36])[N:32]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 15766822HCID 15766822, compound2×HCID 178493561HCID 178493561, compound

Product 1

HCID 18916377HCID 18916377, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5.5 g (25 mmol) of methyl 3-(2-thienyl)-3-fluoro-2-hydroxybutyrate (Compound 1.1) 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 2 hours at room temperature, washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue is taken up in dimethylformamide (DMF), and this is 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 hydrogen carbonate in 100 ml of DMF. After the mixture has been stirred for 2 hours at room temperature and for a further 2 hours at 60° C., the mixture is poured into 1 l of ice-water, and the precipitate which has formed is filtered off with suction. After drying, 2.5 g of a white powder remain.

Workup

  1. stirringThe mixture is stirred for 2 hours at room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. stirringAfter the mixture has been stirred for 2 hours at room temperature and for a further 2 hours at 60° C.
  6. customthe precipitate which has formed
  7. filtrationis filtered off with suction
  8. customAfter drying

Sources & evidence

ORD record
ord-aa86f2314fda4b209eccdf134822e6ea
Source dataset
uspto-grants-1998_05
Patent number
US05753594

Reaction notes

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