Sodium Dithionite → N'-(3-benzyl-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-N,N-dimethylmethanimidamide

HRID 1805855Notes

Reaction equation

HRID 1805855 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([N+]([O-])=O)=[C:11](/[CH:18]=[CH:19]/[N:20](C)C)[N:10]=[C:9]1/[N:23]=[CH:24]/[N:25]([CH3:27])[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C1COCC1>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[NH:20][CH:19]=[CH:18][C:11]=2[N:10]=[C:9]1/[N:23]=[CH:24]/[N:25]([CH3:26])[CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 15376104N'-[1-benzyl-4-[(E)-2-(dimethylamino)ethenyl]-5-nitro-6-oxopyrimidin-2-yl]-N,N-dimethylmethanimidamide

Product 1

HCID 57693601N'-(3-benzyl-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-N,N-dimethylmethanimidamideYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (E)-N′-(1-benzyl-4-((E)-2-(dimethylamino)vinyl)-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl)-N,N-dimethylformimidamide (43.0 g, 0.12 mol) in THF (151 mL) was added an aqueous saturated solution of Na2S2O4 and stirred at room temperature overnight. Upon completion of the reaction, the solid was filtered and washed with THF to afford the product (21.2 g, 62% yield) which was used in the next step without further purification.

Workup

  1. customUpon completion of the reaction
  2. filtrationthe solid was filtered
  3. washwashed with THF

Sources & evidence

ORD record
ord-c3266cc05aff42eaaee90bc1c2fb51ac
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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