Sodium Hydroxide → Ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate

HRID 842056Notes

Reaction equation

HRID 842056 reaction equation
O=[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:3]1.P(Cl)(Cl)([Cl:21])=O.[OH-].[Na+]>>[Cl:21][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 657593Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate

Product 1

HCID 239537Ethyl 4-chloro-2-phenylpyrimidine-5-carboxylateYield 85.2%

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 3,4-dihydro-4-oxo-2-phenylpyrimidine-5-carboxylate (12 g) and phosphorus oxychloride (22.6 g) is stirred at 90° C. for four hours. The reaction mixture is poured into ice-water, and the mixture is neutralized with 1N aqueous sodium hydroxide solution. The precipitates are collected by filtration, and washed with water to give the desired compound (11 g).

Workup

  1. filtrationThe precipitates are collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-23bc35c148d94127b95f433afbde5c26
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

Loading…