Sodium Azide → HCID 22172628, compound

HRID 2055662Notes

Reaction equation

HRID 2055662 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][CH:13]=[CH:14][N:15]=2)[N:10]=[C:9]1[CH:19](Br)[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C>[N:24]([CH:19]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17](=[O:18])[C:16]2[C:11](=[N:12][CH:13]=[CH:14][N:15]=2)[N:10]=1)[CH:20]([CH3:22])[CH3:21])=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 221725823-benzyl-2-(1-bromo-2-methyl-propyl)-3H-pteridin-4-one

Product 1

HCID 22172628HCID 22172628, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Formula 106 where R2 and R3 are H; R5 is Benzyl: R6 is Isopropyl; R6′ is H; X and Y are —C═; and W and Z are —N═: A DMF (50 mL) solution of 3-benzyl-2-(1-bromo-2-methyl-propyl)-3H-pteridin-4-one (1.4 g, 3.75 mmol) and sodium azide (0.488 g, 7.50 mmol) was stirred at 60° C. for two hours and concentrated under reduced pressure. The residue was dissolved in dichloromethane, washed with water and brine, dried over sodium sulfate and concentrated in vacuo to give desired azido product of Formula 106, 2-(1-azido-2-methyl-propyl)-3-benzyl-3H-pteridin-4-one, which was taken on without further purification. MS (Cl) M/E: 336.1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2976f50de5854cb58be43bafcc8ccea8
Source dataset
uspto-grants-2008_02
Patent number
US07332498B2

Reaction notes

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