Morpholine → Chloro-4-morpholino-6-nitro-pyrido[2,3-d]pyrimidine

HRID 1434512Notes

Reaction equation

HRID 1434512 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[N:8][C:6]=2[N:7]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:5]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 860497362,4-Dichloro-6-nitro-pyrido[2,3-d]pyrimidine

Product 1

HCID 57935891Chloro-4-morpholino-6-nitro-pyrido[2,3-d]pyrimidineYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4-Dichloro-6-nitro-pyrido[2,3-d]pyrimidine (5.8 g; 23.8 mmol) was dissolved in dichloromethane (100 mL), and chilled in a dry ice bath. To the cold solution was added morpholine (2.07 g; 23.8 mmol), and diisopropylethylamine (3.07 g; 23.8 mmol) and it was allowed to warm gradually to room temperature. The solution was washed with a saturated ammonium chloride solution (2×50 mL), dried over magnesium sulfate, and evaporated to give 2-chloro-4-morpholino-6-nitro-pyrido[2,3-d]pyrimidine (6.7 g.).

Workup

  1. temperaturechilled in a dry ice bath
  2. washThe solution was washed with a saturated ammonium chloride solution (2×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-a8b7370a0faf455d9e69f5db904a7933
Source dataset
uspto-grants-2009_11
Patent number
US07615552B2

Reaction notes

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