Potassium Carbonate → HCID 59772236, compound

HRID 2220263Notes

Reaction equation

HRID 2220263 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][C:14]=2[CH3:19])[N:3]=1.P(Cl)(Cl)([Cl:22])=O.C(=O)([O-])[O-].[K+].[K+]>>[Cl:22][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][C:14]=2[CH3:19])[N:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 178469735HCID 178469735, compound

Product 1

HCID 59772236HCID 59772236, compoundYield 84%

Conditions

Temperature
-5 °C

Procedure

A solution of 4.00 g of ethyl 4-hydroxy-2-o-tolylpyrimidine-5-carboxylate (15.5 mmol) in 11.6 mL of phosphorous oxychloride (124 mmol) was heated to reflux (calcium chloride filled tube as protection from the outside atmosphere). After 3 h, the excess POCl3 was removed by distillation (˜20 Torr, 90-100° C. oil bath). The residual red oil on cooling solidified. The solids were pulverized and covered with 100 mL of EtOAc. The slurry was cooled to −5° C. and agitated vigorously for 10 min with 25 mL of a potassium carbonate solution (2 M, 50 mmol). The resulting organic phase was separated, dried (MgSO4), filtered and evaporated to give, after triturating in hexanes, the title compound as a light orange solid, 3.58 g, 84% yield.

Workup

  1. temperatureto reflux (calcium chloride filled tube as protection from the outside atmosphere)
  2. customthe excess POCl3 was removed by distillation (˜20 Torr, 90-100° C. oil bath)
  3. temperatureThe residual red oil on cooling
  4. customThe resulting organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give
  9. customafter triturating in hexanes

Sources & evidence

ORD record
ord-587d894a71af4e278551d9700c9cab1e
Source dataset
uspto-grants-2008_08
Patent number
US07417028B2

Reaction notes

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