Sodium Azide → HCID 57929460, compound

HRID 2386664Notes

Reaction equation

HRID 2386664 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[C:6]1[C:15]2[CH:14]=[N:13][C:12]([S:16][CH3:17])=[N:11][C:10]=2[N:9]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8](=[O:23])[CH:7]=1>CN(C=O)C>[N:1]([C:6]1[C:15]2[CH:14]=[N:13][C:12]([S:16][CH3:17])=[N:11][C:10]=2[N:9]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8](=[O:23])[CH:7]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57929477HCID 57929477, compound

Product 1

HCID 57929460HCID 57929460, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Sodium azide (543 mg, 8.35 mmol) was added to a mixture of 5-bromo-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.42 g, 4.17 mmol) in DMF (17 mL) at RT and the reaction mixture was heated to 90° C. in a microwave reactor for 30 min. The resulting mixture was then cooled to RT and quenched with water (70 mL). The solid that formed was collected by filtration, dried under reduced pressure, dissolved in THF and adsorbed onto silica gel. This material was purified by flash chromatography (from 10 to >25% EtOAc/hexanes in 20 min) to afford 0.720 g (57% yield) of 5-azido-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid. MS=303 [M+H]+.

Workup

  1. temperatureThe resulting mixture was then cooled to RT
  2. customquenched with water (70 mL)
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure
  6. dissolutiondissolved in THF
  7. customThis material was purified by flash chromatography (from 10 to >25% EtOAc/hexanes in 20 min)

Sources & evidence

ORD record
ord-c5a572a62c654d34b78b25bc8bbfe0c6
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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