Thionyl Chloride → 2-Acetylamino-4-chloromethylpyrimidine

HRID 1890497Notes

Reaction equation

HRID 1890497 reaction equation
S(Cl)([Cl:3])=O.[C:5]([NH:8][C:9]1[N:14]=[C:13]([CH2:15]O)[CH:12]=[CH:11][N:10]=1)(=[O:7])[CH3:6]>C(Cl)Cl>[C:5]([NH:8][C:9]1[N:14]=[C:13]([CH2:15][Cl:3])[CH:12]=[CH:11][N:10]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 671607102-Acetylamino-4-hydroxymethylpyrimidine

Product 1

HCID 451192602-Acetylamino-4-chloromethylpyrimidineYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.18 mL, 2.4 mmol) was added to a suspension of 2-acetylamino-4-hydroxymethylpyrimidine (290 mg, 1.7 mmol, Reference Compound No. 4-3) in anhydrous methylene chloride (10 mL) at room temperature, and the mixture was stirred for 30 minutes. The solvent was evaporated under reduced pressure, then water (50 mL) and ethyl acetate (100 mL) were added thereto and the mixture was separated into the organic layer and the aqueous layer, and the aqueous layer was extracted twice with ethyl acetate (50 mL). The whole organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 68 mg of the title Reference Compound as a yellow solid (Yield: 18%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionwater (50 mL) and ethyl acetate (100 mL) were added
  3. customthe mixture was separated into the organic layer
  4. extractionthe aqueous layer, and the aqueous layer was extracted twice with ethyl acetate (50 mL)
  5. dry with materialThe whole organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d44576f89354420fbe5e07e0fd4be289
Source dataset
uspto-grants-2013_08
Patent number
US08507485B2

Reaction notes

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