2-Morpholinoethanol → 4-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-nitro-pyrido[2,3-d]pyrimidine

HRID 1879820Notes

Reaction equation

HRID 1879820 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[N:8][C:6]=2[N:7]=1.[O:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][OH:29])[CH2:23][CH2:22]1.[Na]>O1CCCC1>[N:15]1([C:4]2[C:5]3[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[N:8][C:6]=3[N:7]=[C:2]([O:29][CH2:28][CH2:27][N:24]3[CH2:25][CH2:26][O:21][CH2:22][CH2:23]3)[N:3]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 611632-MorpholinoethanolHCID 5360545SodiumHCID 57935891Chloro-4-morpholino-6-nitro-pyrido[2,3-d]pyrimidine

Product 1

HCID 689208664-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-nitro-pyrido[2,3-d]pyrimidineYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chloro-4-morpholino-6-nitro-pyrido[2,3-d]pyrimidine (4.4 g; 15 mmol) was dissolved in tetrahydrofuran (100 mL). To the solution was added morpholino-2-ethanol (2.4 g; 18 mmol), and it was chilled in a dry ice bath. Sodium 400 mg; 18 mmol) was then added, and it was allowed to warm to room temperature and stirred overnight. The solvent was then evaporated, and the solid was dissolved in dichloromethane (50 mL), washed with water (3×10 mL), dried over magnesium sulfate, and purified by column chromatography to give 4-morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-nitro-pyrido[2,3-d]pyrimidine (3.35 g).

Workup

  1. temperaturewas chilled in a dry ice bath
  2. addition18 mmol) was then added
  3. customThe solvent was then evaporated
  4. dissolutionthe solid was dissolved in dichloromethane (50 mL)
  5. washwashed with water (3×10 mL)
  6. dry with materialdried over magnesium sulfate
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-e21c44b91f9e4eda87fe5e99a3b81869
Source dataset
uspto-grants-2012_11
Patent number
US08318730B2

Reaction notes

Loading…