Sodium Hydroxide → HCID 57600200, compound

HRID 1664548Notes

Reaction equation

HRID 1664548 reaction equation
[Cl-].Cl[C:3](Cl)=[N+:4]([CH3:6])[CH3:5].[CH2:8]([N:13]1[C:21]2[N:20]=[CH:19][NH:18][C:17]=2[C:16](=[O:22])[NH:15]/[C:14]/1=[N:23]/[NH2:24])[CH2:9][CH2:10][CH2:11][CH3:12].[OH-].[Na+]>C(Cl)Cl>[CH3:5][N:4]([CH3:6])[C:3]1[N:15]2[C:16](=[O:22])[C:17]3[NH:18][CH:19]=[N:20][C:21]=3[N:13]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:14]2=[N:23][N:24]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723945Phosgeniminium chlorideHCID 178446165HCID 178446165, compound

Product 1

HCID 57600200HCID 57600200, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methylene chloride (10 mL) was added [B] N-(dichloromethylene)-N-methylmethanaminium chloride (0.21 g, 1.3 mmol). After stirring for 5 mins, (2Z)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (0.10 g, 0.42 mmol) was added, and the mixture was stirred at rt for 5 hrs. LCMS analysis showed product as a major peak was formed. 1N NaOH was carefully added to neutralize the acid, and the mixture was extracted with methylene chloride three times. The combined organic layers were dried by MgSO4, filtered and concentrated in vacuo to yield the desired product (84 mg, 69%). LCMS calculated for C13H20N7O (M+H): 290.2. found 290.1.

Workup

  1. stirringthe mixture was stirred at rt for 5 hrs
  2. customwas formed
  3. extractionthe mixture was extracted with methylene chloride three times
  4. dry with materialThe combined organic layers were dried by MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ed951a719c046748f43a78613d278aa
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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