Ethylene Glycol → 6-(2-Hydroxy-ethoxy)-2-phenyl-pyrimidine-4-carboxylic acid

HRID 553816Notes

Reaction equation

HRID 553816 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].Cl[C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]([C:20]([OH:22])=[O:21])[CH:9]=1.Cl>C1COCC1>[OH:3][CH2:2][CH2:1][O:4][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]([C:20]([OH:22])=[O:21])[CH:9]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 574316986-Chloro-2-phenylpyrimidine-4-carboxylic acid

Product 1

HCID 674623456-(2-Hydroxy-ethoxy)-2-phenyl-pyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethylene glycol (34 μl) was added to a suspension of sodium hydride (24 mg) in anhydrous THF (2 ml) at 0° C. After 30 min stirring at 0° C., 6-chloro-2-phenyl-pyrimidine-4-carboxylic acid (47 mg) dissolved in THF (1.2 ml) was added. The mixture was allowed to warm to RT and stirred overnight. A 1M HCl solution was added and the resulting mixture was extracted with EA. The org. phases were dried (Na2SO4) and evaporated off.

Workup

  1. additionwas added
  2. temperatureto warm to RT
  3. stirringstirred overnight
  4. extractionthe resulting mixture was extracted with EA
  5. dry with materialphases were dried (Na2SO4)
  6. customevaporated off

Sources & evidence

ORD record
ord-94301cc1471848a0bfb7295c3e933394
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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