Water → 4-Chloro-6-ethoxy-2-(methylthio)pyrimidine

HRID 1455217

Reaction equation

HRID 1455217 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[O-:11][CH2:12][CH3:13].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:11][CH2:12][CH3:13])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 2723922Sodium ethoxide

Product 1

HCID 533855534-Chloro-6-ethoxy-2-(methylthio)pyrimidineYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4,6-dichloro-2-methylsulfanylpyrimidine (500 mg, 2.56 mmol) in anhydrous DMF (6 mL) was added sodium ethoxide (174 mg, 2.56 mmol). The reaction mixture was stirred at 70° C. for overnight. The resulting mixture was poured into 30 mL of water and was extracted with diethyl ether (20 mL×3) three times. The ether layer was separated and dried with anhydrous MgSO4 and concentrated in vacuo to give crude product 4-chloro-6-ethoxy-2-methylsulfanylpyrimidine (525 mg). 1H-NMR (CDCl3): δ 6.39 (s, 1 H), 4.43 (q, J=7.1 Hz, 2 H), 2.54 (s, 3 H), 1.38 (t, J=7.1 H, 3 H).

Workup

  1. extractionwas extracted with diethyl ether (20 mL×3) three times
  2. customThe ether layer was separated
  3. dry with materialdried with anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3348b65579aa42ecbe78d3c57af15b9a
Source dataset
uspto-grants-2009_01
Patent number
US07482366B2

Linked notes

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