Hydrochloric Acid → N'-(1-benzyl-4-methyl-5-nitro-6-oxopyrimidin-2-yl)-N,N-dimethylmethanimidamide

HRID 1516833Notes

Reaction equation

HRID 1516833 reaction equation
[CH3:1][N:2]([CH3:16])/[CH:3]=[N:4]/[C:5]1[NH:6][C:7](=[O:15])[C:8]([N+:12]([O-:14])=[O:13])=[C:9]([CH3:11])[N:10]=1.C1CCN2C(=NCCC2)CC1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>CN(C=O)C>[CH2:28]([N:6]1[C:7](=[O:15])[C:8]([N+:12]([O-:14])=[O:13])=[C:9]([CH3:11])[N:10]=[C:5]1/[N:4]=[CH:3]/[N:2]([CH3:1])[CH3:16])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 1355361192-[(Dimethylamino)methylene]amino-6-methyl-5-nitro-4-pyrimidinol

Product 1

HCID 11186127N'-(1-benzyl-4-methyl-5-nitro-6-oxopyrimidin-2-yl)-N,N-dimethylmethanimidamideYield 85,493.203%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (E)-N,N-Dimethyl-N′-(4-methyl-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl)formimidamide (53.4 g, 0.24 mmol) in DMF (690 mL) was added DBU (44.6 mL, 0.30 mol) and benzyl bromide (44.4 mL, 0.29 mol) and stirred at room temperature for 1 h. The excess of DBU was neutralized with HCl, and the mixture was concentrated in vacuo. The residue was dissolved in methylene chloride and extracted twice with 2M HCl and water, then dried over Na2SO4 and concentrated. Trituration with ethanol afforded the crystalline product which was washed with ethanol to give the product (64.7 g, 86% yield) and used in the next step without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. extractionextracted twice with 2M HCl and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customTrituration with ethanol afforded the crystalline product which
  7. washwas washed with ethanol

Sources & evidence

ORD record
ord-7c64de0dd6be42b994556cd9606e58ab
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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