Monoperoxyphthalic Acid Magnesium Salt → 3-Methyl-6-(2-methylsulfinylethyl)-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione

HRID 742970Notes

Reaction equation

C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:5].[Mg+2].[CH3:15][N:16]1[C:21](=[O:22])[C:20]2[CH2:23][N:24]([CH2:27][CH2:28][S:29][CH3:30])[CH2:25][CH2:26][C:19]=2[NH:18][C:17]1=[O:31]>C(O)C>[CH3:15][N:16]1[C:21](=[O:22])[C:20]2[CH2:23][N:24]([CH2:27][CH2:28][S:29]([CH3:30])=[O:5])[CH2:25][CH2:26][C:19]=2[NH:18][C:17]1=[O:31]

Participants

Conditions

Temperature: 55 °C

Procedure

21.8 g of magnesium monoperoxyphthalate (85% pure) were added at 55° C. over a period of 15 min to a solution of 19.5 g of 3-methyl-6-(2-methylsulfanylethyl)-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione in 200 ml of ethanol and the mixture was stirred for 2 h at 55° C. After the pH had been adjusted to 7.5, the mixture was concentrated under reduced pressure. The residue was boiled up several times with methanol, the combined methanol phases were concentrated and the residue was purified by chromatography in a medium-pressure column with silica gel using dichloromethane/methanol (volume ratio 95:5) as the eluent and by recrystallization from isopropanol.

Workup

concentrationthe mixture was concentrated under reduced pressure
concentrationthe combined methanol phases were concentrated
customthe residue was purified by chromatography in a medium-pressure column with silica gel
customby recrystallization from isopropanol

Sources & evidence

ORD record: ord-f5c4cc555ad7444194912a8cd30088a2
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556854

Reaction notes

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