Ethyl Glycolate → (6-Chloro-2-morpholin-4-yl-pyrimidin-4-yloxy)-acetic acid ethyl ester

HRID 882748

Reaction equation

HRID 882748 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11](Cl)[CH:10]=[C:9]([Cl:14])[N:8]=2)[CH2:3][CH2:2]1.[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:16][OH:17].[H-].[Na+]>O1CCCC1>[CH2:20]([O:19][C:15](=[O:18])[CH2:16][O:17][C:11]1[CH:10]=[C:9]([Cl:14])[N:8]=[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[N:12]=1)[CH3:21]

Participants

5

Reactant 3

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 27720684-(4,6-Dichloropyrimidin-2-yl)morpholine

Product 1

HCID 86243996(6-Chloro-2-morpholin-4-yl-pyrimidin-4-yloxy)-acetic acid ethyl esterYield 104.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Morpholino-4,6-dichloropyrimidine (2.34 g; 10 mmol) and ethyl glycolate (1.3 g; 12 mmol) were dissolved in tetrahydrofuran (100 mL), and chilled in an ice bath. To the solution was added sodium hydride (300 mg; 12 mmol), and it was stirred overnight at ambient temperature. The solvents were evaporated, and the solid was dissolved in ethyl acetate (200 mL) which was then washed with water (2×100 mL). The organic layer was dried over magnesium sulfate, and evaporated to give (6-chloro-2-morpholin-4-yl-pyrimidin-4-yloxy)-acetic acid ethyl ester (3.16 g).

Workup

  1. temperaturechilled in an ice bath
  2. customThe solvents were evaporated
  3. dissolutionthe solid was dissolved in ethyl acetate (200 mL) which
  4. washwas then washed with water (2×100 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-650da53bd7734004811cdcd2406ddb9c
Source dataset
uspto-grants-2012_08
Patent number
US08236795B2

Linked notes

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