2-[(5-Dimethylaminomethyl-3-thienyl)methylthio]ethylamine → 5-Nitro-2-{2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamino}-4(3H)-pyrimidone

HRID 622783Notes

Reaction equation

HRID 622783 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:9][CH:8]=[C:7]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[CH:6]=1)[CH3:3].CS[C:17]1[N:22]=[C:21]([OH:23])[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1>C(O)C>[N+:24]([C:20]1[C:21](=[O:23])[NH:22][C:17]([NH:14][CH2:13][CH2:12][S:11][CH2:10][C:7]2[CH:6]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[S:9][CH:8]=2)=[N:18][CH:19]=1)([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 129265012-[(5-Dimethylaminomethyl-3-thienyl)methylthio]ethylamineHCID 178503473C5H5N3O3S

Product 1

HCID 143266985-Nitro-2-{2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamino}-4(3H)-pyrimidoneYield 63.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamine (2.88 g; 12.5 mmoles) and 2-methylthio-5-nitro-4-hydroxypyrimidine (2.33 g; 12.44 mmoles) in 10 ml of ethanol was heated at reflux temperature for 13 hours. The reaction mixture was evaporated under reduced pressure, and the residue was placed on 150 g of silica gel and chromatographed by flash chromatography using a gradient elution of methanol-methylene chloride. The appropriate fractions gave 2.92 g of product which was recrystallized from tetrahydrofuran to give the title compound, mp 150°-153° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 13 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customchromatographed by flash chromatography
  5. washa gradient elution of methanol-methylene chloride

Sources & evidence

ORD record
ord-c98a860dbaaa4c35b8ba467094606c8c
Source dataset
uspto-grants-1988_09
Patent number
US04772704

Reaction notes

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