Water → HCID 86657915, compound

HRID 2359019Notes

Reaction equation

HRID 2359019 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[S:14][C:13]([C:15](OCC)=[O:16])=[CH:12][CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O>C1COCC1.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:15]([C:13]2[S:14][C:10]([Cl:9])=[CH:11][CH:12]=2)=[O:16])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 521808Ethyl 5-chlorothiophene-2-carboxylateHCID 2733832Lithium HexamethyldisilazideHCID 116296072-Chloro-4-methylpyrimidine

Product 1

HCID 86657915HCID 86657915, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2-chloro-4-methylpyrimidine (1 eq, 46.7 mmol) and ethyl 5-chlorothiophene-2-carboxylate (1.1 eq, 51.3 mmol) in anhydrous THF (50 mL) at 0° C., under N2 was added dropwise a solution of lithium bis(trimethylsilyl)amide (1 molar solution in hexanes, 2 eq, 93.3 mmol). The mixture was stirred 2 h at 5° C. Water was then added followed by 300 mL of dichloromethane. The organic layer was separated and the yellow precipitate was then filtered and dried to afford 10.7 g (84% yield) of 2-(2-chloropyrimidin-4-yl)-1-(5-chloro-2-thienyl)ethanone.

Workup

  1. customThe organic layer was separated
  2. filtrationthe yellow precipitate was then filtered
  3. customdried

Sources & evidence

ORD record
ord-1df0aefb2c9c4aed984d068dfe751e8f
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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