Phosphorus oxychloride → Ethyl 4-chloro-2-(dimethylamino)pyrimidine-5-carboxylate
Reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[N:8]=[C:7](O)[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][N:4]=1.P(Cl)(Cl)([Cl:18])=O>>[CH3:1][N:2]([CH3:15])[C:3]1[N:8]=[C:7]([Cl:18])[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][N:4]=1Participants
Procedure
A suspension of 16 g of 2-dimethylamino-4-hydroxy-5-carboethoxy-pyrimidine in 100 ml of phosphorous oxychloride is heated to the boil for half an hour whilst stirring and is then filtered hot, and the filtrate is evaporated under reduced pressure. 200 g of ice are added to the oily residue. 200 ml of methylene chloride are added and 30% strength sodium hydroxide solution is then added, whilst cooling with ice, until the pH reaches 8. Inorganic salts which have precipitated are then filtered off and rinsed with methylene chloride. The organic phase is washed with water, dried over sodium sulphate and evaporated. 2-Dimethylamino-4-chloro-5-carboethoxypyrimidine is obtained as a yellowish oil which can be used further without purification.
Workup
- temperatureis heated to the boil for half an hour
- filtrationis then filtered hot
- customthe filtrate is evaporated under reduced pressure
- addition200 g of ice are added to the oily residue
- addition200 ml of methylene chloride are added
- addition30% strength sodium hydroxide solution is then added
- temperaturewhilst cooling with ice, until the pH
- customInorganic salts which have precipitated
- filtrationare then filtered off
- washrinsed with methylene chloride
- washThe organic phase is washed with water
- dry with materialdried over sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-07c73572df81486da807399f653a2a73
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04115575
Reaction notes
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