Phosphorus oxychloride → 4-Chloro-5-iodo-6-methylpyrimidine

Reaction equation

O[C:2]1[C:7]([I:8])=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=1.O=P(Cl)(Cl)[Cl:12]>>[Cl:12][C:2]1[C:7]([I:8])=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 1784332135-iodo-6-methyl-1H-pyrimidin-4-one

Product 1

HCID 127953694-Chloro-5-iodo-6-methylpyrimidine

Conditions

Temperature: 90 °C

Procedure

A suspension of 90 g (0.38 mol) 4-hydroxy-5-iodo-6-methylpyrimidine in 600 mL POCl3 is heated for 1 h at 90° C. The reaction mixture is concentrated under reduced pressure and the residue is poured into crushed ice. The precipitated solid is collected by filtration and washed with water. After drying, the desired product is obtained as a solid (90 g; 93%).

Workup

concentrationThe reaction mixture is concentrated under reduced pressure
additionthe residue is poured
custominto crushed ice
filtrationThe precipitated solid is collected by filtration
washwashed with water
customAfter drying

Sources & evidence

ORD record: ord-d1874e923c3542ddbff6f02ee3635455
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633183B2

Reaction notes

Loading…