Sodium Azide → 2-(1-azidopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1429772Notes

Reaction equation

HRID 1429772 reaction equation
Br[CH:2]([C:5]1[N:6]=[C:7]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:8]2[C:9](=[O:12])[C:10]=1[I:11])[CH2:3][CH3:4].[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:18]([CH:2]([C:5]1[N:6]=[C:7]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:8]2[C:9](=[O:12])[C:10]=1[I:11])[CH2:3][CH3:4])=[N+:19]=[N-:20]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 668641442-(1-bromopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 866500622-(1-azidopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(1-bromopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (4.50 g, 11.0 mmol) and sodium azide (3.59 g, 55.3 mmol) in DMF was stirred at room temperature for 2 h. After diluting with ethyl acetate, the mixture was washed with water, brine, dried over sodium sulfate, and evaporated under reduced pressure to provide the crude product, which was used directly in next step (3.35 g, 82.1%). LCMS calculated for C12H13IN5O (M+H)+: m/z=370.0. Found: 370.2.

Workup

  1. washthe mixture was washed with water, brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-66a02c7ea8b34a439ffc43983c506df2
Source dataset
uspto-grants-2015_01
Patent number
US08940752B2

Reaction notes

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