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

HRID 1434513Notes

Reaction equation

HRID 1434513 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. additionwas 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-a0cf3da491374d9eac64f48ab423b8bf
Source dataset
uspto-grants-2009_11
Patent number
US07615552B2

Reaction notes

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