Dichloromethane → 2-(1-aminopropyl)-6-methyl-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1429774Notes

Reaction equation

HRID 1429774 reaction equation
[N:1]([CH:4]([C:7]1[N:8]=[C:9]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:10]2[C:11](=[O:19])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][CH3:6])=[N+]=[N-].CP(C)C.C(Cl)Cl>O1CCCC1.O>[NH2:1][CH:4]([C:7]1[N:8]=[C:9]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:10]2[C:11](=[O:19])[C:12]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 68983TrimethylphosphineHCID 866500632-(1-azidopropyl)-6-methyl-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 668636882-(1-aminopropyl)-6-methyl-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-(1-azidopropyl)-6-methyl-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one (0.030 g, 0.094 mmol) in tetrahydrofuran (0.24 mL) and water (0.06 mL) was added 1.0 M of trimethylphosphine in tetrahydrofuran (0.11 mL) at room temperature and the mixture was stirred at room temperature for 1 hour. To the mixture was added methylene chloride and the mixture was washed with brine, dried over magnesium sulfate, and evaporated to dryness under reduced pressure. The crude residue was used directly in next step. LCMS calculated for C18H20N3O (M+H)+: m/z=294.2. Found: 294.3.

Workup

  1. washthe mixture was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e8c156d06a6048e0a6c86e6b61740d74
Source dataset
uspto-grants-2015_01
Patent number
US08940752B2

Reaction notes

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