Thionyl Chloride → 1,3-Diethyl-8-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-3,7-dihydro-purine-2,6-dione

HRID 1262523Notes

Reaction equation

HRID 1262523 reaction equation
[CH2:1]([N:3]1[C:11](=[O:12])[C:10]2[NH:9][C:8]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([OH:22])(=O)=[O:20])=[CH:15][CH:14]=3)=[N:7][C:6]=2[N:5]([CH2:23][CH3:24])[C:4]1=[O:25])[CH3:2].S(Cl)(Cl)=O.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>CN(C)C=O>[CH2:1]([N:3]1[C:11](=[O:12])[C:10]2[NH:9][C:8]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([N:34]4[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]4)(=[O:20])=[O:22])=[CH:17][CH:18]=3)=[N:7][C:6]=2[N:5]([CH2:23][CH3:24])[C:4]1=[O:25])[CH3:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 531671-MethylpiperazineHCID 155873004-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid

Product 1

HCID 155873071,3-Diethyl-8-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-3,7-dihydro-purine-2,6-dioneYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid (5.0 g, 0.014 moles) and N,N-dimethylformamide (150 ml) is cooled to 0° and treated with thionyl chloride (3.3 g, 0.027 moles). When the addition is complete, the reaction mixture is permitted to warm to ambient temperature and stirred vigorously until a thick slurry results. To this slurry is added N-methylpiperazine (13.7 g, 0.137 moles) in one portion, the mixture is stirred until a clear solution is obtained, and concentrated on a rotary evaporator. The residue is taken up in water, filtered, recrystallized from ethanol, and dried at 48° to yield 5.12 grams of 1-[[4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)phenyl]sulfonyl]4-methylpiperazine, mp 305°-307° C.

Workup

  1. temperatureis cooled to 0°
  2. additionWhen the addition
  3. customresults
  4. stirringthe mixture is stirred until a clear solution
  5. customis obtained
  6. concentrationconcentrated on a rotary evaporator
  7. filtrationfiltered
  8. customrecrystallized from ethanol
  9. customdried at 48°

Sources & evidence

ORD record
ord-00f000f3c47d4b03b7983fd1f44db36d
Source dataset
uspto-grants-1984_06
Patent number
US04452788

Reaction notes

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