Phosphorus oxychloride → 2-(4-(2-Amino-4-chloro-6-methylpyrimidin-5-ylthio)phenyl)acetonitrile

HRID 2387908Notes

Reaction equation

HRID 2387908 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[C:5]([S:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[CH:12][CH:11]=2)=[C:4]([CH3:19])[N:3]=1.O=P(Cl)(Cl)[Cl:22]>>[NH2:1][C:2]1[N:7]=[C:6]([Cl:22])[C:5]([S:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[CH:12][CH:11]=2)=[C:4]([CH3:19])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178433378HCID 178433378, compound

Product 1

HCID 866334172-(4-(2-Amino-4-chloro-6-methylpyrimidin-5-ylthio)phenyl)acetonitrile

Procedure

A mixture of the product from step (iii) (2.3 g) and POCl3 (25 ml) was heated under reflux for 8 h. The mixture was evaporated under reduced pressure and ice/water added to the residue. The mixture was stirred at rt for 15 min then neutralised with aq. 2M NaOH solution and heated at 40° C. for 2 h then extracted with DCM. The organics were dried, evaporated under reduced pressure and the residue purified by column chromatography (2% MeOH/DCM), to give the subtitle compound as a solid, 530 mg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 h
  3. customThe mixture was evaporated under reduced pressure and ice/water
  4. additionadded to the residue
  5. temperatureheated at 40° C. for 2 h
  6. extractionthen extracted with DCM
  7. customThe organics were dried
  8. customevaporated under reduced pressure
  9. customthe residue purified by column chromatography (2% MeOH/DCM)

Sources & evidence

ORD record
ord-e85ac8d282cf4125aa181b82cc44ef48
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

Loading…