Phosphorus oxychloride → Ethyl 4-chloro-2-(pyrimidin-2-yl)pyrimidine-5-carboxylate

HRID 1005978Notes

Reaction equation

HRID 1005978 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](O)=[N:8][C:9]([C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2].C([O-])(O)=O.[Na+].O=P(Cl)(Cl)[Cl:26]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:26])=[N:8][C:9]([C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178469751HCID 178469751, compound

Product 1

HCID 53396476Ethyl 4-chloro-2-(pyrimidin-2-yl)pyrimidine-5-carboxylateYield 82%

Procedure

A suspension of 1.62 g (6.5 mmol) 4-hydroxy-[2,2′]bipyrimidinyl-5-carboxylic acid ethyl ester in 16 ml POCl3 was heated at reflux for lh. The solution was cooled to RT and poured into 100 ml ice-water. The pH of the solution was adjusted to 8 with sat. NaHCO3-solution. The water phase was extracted three times with 80 ml CH2Cl2. The combined organic phases were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 95:5) to give 1.43 g (82%) 4-chloro-[2,2′]bipyrimidinyl-5-carboxylic acid ethyl ester as a light brown solid, MS (EI): 264.1 (M+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for lh
  3. extractionThe water phase was extracted three times with 80 ml CH2Cl2
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-2cc52ee50edf4bddbe276f48d26b1a85
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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