Dimethylformamide → 2-Chloro-5-(3-thienylmethoxy)pyrimidine

HRID 1082318Notes

Reaction equation

HRID 1082318 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.Cl[CH2:10][C:11]1[CH:15]=[CH:14][S:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:10][C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 124874623-(Chloromethyl)thiopheneHCID 145957002-Chloro-5-pyrimidinol

Product 1

HCID 196895222-Chloro-5-(3-thienylmethoxy)pyrimidineYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-5-hydroxypyrimidine (200 mg), 3-chloromethylthiophene (610 mg), potassium carbonate (635 mg) and dimethylformamide (3 ml) is stirred at 50° C. for one hour. After the reaction is complete, to the reaction mixture is added water, and extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=20:1→20:3), and evaporated to remove the solvent to give 2-chloro-5-(3-thienylmethoxy)pyrimidine (345 mg) as colorless needles.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=20:1→20:3)
  6. customevaporated
  7. customto remove the solvent

Sources & evidence

ORD record
ord-177c57a0422b44a2aa2df8f123354464
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Reaction notes

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