Phosphorus oxychloride → 4-Chloro-2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidine

HRID 1508719Notes

Reaction equation

HRID 1508719 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[NH:8][C:9](=O)[C:10]([CH2:14][CH3:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:9]1[C:10]([CH2:14][CH3:15])=[C:11]([CH3:13])[N:12]=[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1359966122-(5-chloro-2-thienyl)-5-ethyl-4-methyl-1H-pyrimidin-6-one

Product 1

HCID 610002304-Chloro-2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidineYield 66%

Procedure

An 100-mL round bottomed flask was charged 2-(5-Chloro-2-thienyl)-5-ethyl-4-methyl-1H-pyrimidin-6-one (4 g, 15.7 mmol). POCl3 (16 ml) was added. The resulting mixture was stirred at 90 C for 6 hr. After cooling to room temperature, the volatile material was removed under reduced pressure and the residue was with NaHCO3 aq (100 ml). Dichloromethane was added. The organic layer was separated and passed through a plug of silica gel, using dichloromethane as eluent to give the title compound as a solid (2.82 g, 66% yield).

Workup

  1. customthe volatile material was removed under reduced pressure
  2. additionDichloromethane was added
  3. customThe organic layer was separated

Sources & evidence

ORD record
ord-8000bc6ad3044a4bbd0a80893652f68f
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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