Phosphorus oxychloride → HCID 178447933, compound

HRID 1463008Notes

Reaction equation

HRID 1463008 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@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]2)[N:3]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178447935HCID 178447935, compound

Product 1

HCID 178447933HCID 178447933, compound

Procedure

32.85 g of ethyl trans-4-hydroxy-2-(4-propylcyclohexyl)-5-pyrimidinecarboxylate are boiled under reflux for 3.5 hours with 210 ml of phosphorus oxychloride. After cooling, the mixture is concentrated in vacuo and evaporated twice further with 100 ml of toluene each time. The residue is chromatographed with methylene chloride on a column of 300 g of silica gel. There are obtained 31.3 g of crude ethyl trans-4-chloro-2-(4-propylcyclohexyl)-5-pyrimidinecarboxylate as a yellow oil.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated in vacuo
  3. customevaporated twice further with 100 ml of toluene each time
  4. customThe residue is chromatographed with methylene chloride on a column of 300 g of silica gel

Sources & evidence

ORD record
ord-a153dde10f9147d1bf99d5c19ac305c1
Source dataset
uspto-grants-1984_07
Patent number
US04462923

Reaction notes

Loading…