N-Iodosuccinimide → 2-(1-bromopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 58224Notes

Reaction equation

HRID 58224 reaction equation
[Br:1][CH:2]([C:5]1[N:6]=[C:7]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:8]2[C:9](=[O:11])[CH:10]=1)[CH2:3][CH3:4].[I:17]N1C(=O)CCC1=O>C(#N)C>[Br:1][CH:2]([C:5]1[N:6]=[C:7]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:8]2[C:9](=[O:11])[C:10]=1[I:17])[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 668642082-(1-bromopropyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 668641442-(1-bromopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneYield 90.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(1-bromopropyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (3.46 g, 12.3 mmol) and N-iodosuccinimide (4.15 g, 18.4 mmol) in acetonitrile (100 mL) was stirred at 80° C., under nitrogen, overnight. After removal of acetonitrile in vacuum, the resulting solid was dissolved in methylene chloride, washed with water, saturated Na2S2O3, saturated sodium bicarbonate, and brine; and then the organic layers dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure to provide the desired product (4.53 g, 90.4%). LCMS calculated for C12H13BrIN2O (M+H)+: m/z=406.9. Found: 407.1.

Workup

  1. customAfter removal of acetonitrile in vacuum
  2. dissolutionthe resulting solid was dissolved in methylene chloride
  3. washwashed with water, saturated Na2S2O3, saturated sodium bicarbonate, and brine
  4. dry with materialand then the organic layers dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a1a37df2a7c047c4a48b07db83119876
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Reaction notes

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