Sodium hydride → 4-[2-(4-Chloro-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholine

HRID 2384503Notes

Reaction equation

HRID 2384503 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11](Cl)[N:10]=[C:9]([Cl:14])[CH:8]=2)[CH2:3][CH2:2]1.[OH:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[H-].[Na+]>O1CCCC1>[Cl:14][C:9]1[CH:8]=[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[N:12]=[C:11]([O:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 611632-MorpholinoethanolHCID 115866994-(2,6-Dichloropyrimidin-4-yl)morpholine

Product 1

HCID 580857604-[2-(4-Chloro-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholineYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Morpholino-2,4-dichloropyrimidine (4.6 g; 20 mmol) and 4-(2-hydroxyethyl)-morpholine (3.3 g; 25 mmol) were dissolved in tetrahydrofuran (200 mL), and chilled in an ice bath. To the solution was added sodium hydride (600 mg; 25 mmol), and it was stirred overnight at room temperature. The solvents were evaporated, and the solid was dissolved in dichloromethane (200 mL) which was then washed with water (2×100 mL). The organic layer was dried over magnesium sulfate, evaporated, and purified by column chromatography to give 4-[2-(4-Chloro-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholine (4.5 g).

Workup

  1. temperaturechilled in an ice bath
  2. customThe solvents were evaporated
  3. dissolutionthe solid was dissolved in dichloromethane (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
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-552cd0b0f51247288cc9e64c1a9118ac
Source dataset
uspto-grants-2012_09
Patent number
US08263764B2

Reaction notes

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