4,6-Dichloro-2[[(4-methoxyphenyl)methyl]thio]pyrimidine → HCID 86663938, compound

HRID 2276289Notes

Reaction equation

HRID 2276289 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1.[CH3:19][NH2:20].CO>>[Cl:8][C:6]1[CH:7]=[C:2]([NH:20][CH3:19])[N:3]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:5]=1

Participants

3

Reactant 2

HCID 134137244,6-Dichloro-2[[(4-methoxyphenyl)methyl]thio]pyrimidineHCID 57454252Monomethylamine methanol

Product 1

HCID 86663938HCID 86663938, compoundYield 56%

Procedure

4,6-dichloro-2-(4-methoxybenzylsulfanyl)pyrimidine (3.0 g, 10 mmol) was dissolved in a 40% methylamine-methanol solution (20 ml) and stirred overnight at room temperature. The solvent was distilled away under reduced pressure, water was added and extracted twice with ethyl acetate. After combining the organic layers and washing with a saturated saline solution, it was dried with MgSO4 and the solvent was distilled away under reduced pressure. Separation and purification were performed by silica gel column chromatography (hexane:ethyl acetate=1:2) to obtain 1.64 g (56% yield) of 4-chloro-2-(4-methoxybenzylsulfanyl)-6-methylaminopyrimidine.

Workup

  1. distillationThe solvent was distilled away under reduced pressure, water
  2. additionwas added
  3. extractionextracted twice with ethyl acetate
  4. washwashing with a saturated saline solution, it
  5. dry with materialwas dried with MgSO4
  6. distillationthe solvent was distilled away under reduced pressure
  7. customSeparation and purification

Sources & evidence

ORD record
ord-759126c57e974218b5576606929d5b00
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Reaction notes

Loading…