Hydrogen Peroxide → 1-[3-(1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dion-7-yl)-2-hydroxypropyl]-4-(3-phenylsulfinylpropyl)piperazine

HRID 1193490Notes

Reaction equation

Cl.[CH3:2][N:3]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][CH:14]([OH:32])[CH2:15][N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][S:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:18][CH2:17]3)[CH:8]=[N:7][C:6]=2[N:5]([CH3:33])[C:4]1=[O:34].[OH:35]O>O.C(Cl)Cl.CO.[NH4+].[OH-]>[CH3:2][N:3]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][CH:14]([OH:32])[CH2:15][N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][S:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:35])[CH2:18][CH2:17]3)[CH:8]=[N:7][C:6]=2[N:5]([CH3:33])[C:4]1=[O:34]

Participants

Conditions

Temperature: 20 °C

Procedure

0.1 Moles of 1-[3-(1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dion-7-yl)-2-hydroxypropyl]-4-(3-phenylthio-propyl)piperazine hydrochloride was dissolved in 200 ml demineralized water and maintained at 20° C. 120 ml hydrogen peroxide in 250 ml water was added dropwise. The mixture was stirred for four hours at room temperature. Completion of the reaction was checked by TLC using a mixture of 80/20/1 CH2Cl2 /methanol/NH4OH as eluent. When the reaction was completed, the reactive mixture was alkalinized, extracted with methylene chloride, washed with water, dried, and the solvent evaporated under vacuum to give the free base form of 1-[3-(1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dion-7-yl)-2-hydroxypropyl]-4-(3-phenylsulfinylpropyl)piperazine. The dihydrochloride salt was prepared in the manner indicated in Example III, m.p. 260°-265° C.

Workup

extractionextracted with methylene chloride
washwashed with water
customdried
customthe solvent evaporated under vacuum

Sources & evidence

ORD record: ord-072b47ad053043948c30d126008b7019
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04810706

Reaction notes

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