Dimethylformamide → 1,3-Diethyl-8-[4-(morpholine-4-sulfonyl)-phenyl]-3,7-dihydro-purine-2,6-dione

HRID 1262524Notes

Reaction equation

HRID 1262524 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](O)(=[O:21])=[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].CN(C)C=O.S(Cl)(Cl)=O.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>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:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)(=[O:20])=[O:21])=[CH:17][CH:18]=3)=[N:7][C:6]=2[N:5]([CH2:23][CH3:24])[C:4]1=[O:25])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 155873004-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid

Product 1

HCID 155873081,3-Diethyl-8-[4-(morpholine-4-sulfonyl)-phenyl]-3,7-dihydro-purine-2,6-dioneYield 54.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 morpholine (20 g, 0.23 moles) in one portion. The resulting slurry is stirred one hour and poured into two liters of water. The resulting suspension is filtered, triturated with ethanol, and dried at 68° to yield 3.29 grams of 4-[[4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)phenyl]sulfonyl]morpholine, mp 354°-355° C.(d).

Workup

  1. temperatureis cooled to 0°
  2. additionWhen the addition
  3. customresults
  4. stirringThe resulting slurry is stirred one hour
  5. filtrationThe resulting suspension is filtered
  6. customtriturated with ethanol
  7. customdried at 68°

Sources & evidence

ORD record
ord-5e5d18ea53c3457f870e52e93de46733
Source dataset
uspto-grants-1984_06
Patent number
US04452788

Reaction notes

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