7-(2,4-Dimethoxybenzyl)-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,5,6,7-tetrahydropyrido[3,4-d]pyrimidine-4,8-dione → 2-(Ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,5,6,7-tetrahydropyrido[3,4-d]pyrimidine-4,8-dione

HRID 570729Notes

Reaction equation

COC1C=C(OC)C=CC=1C[N:6]1[CH2:15][CH2:14][C:13]2[C:12](=[O:16])[N:11]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:19][CH:18]=3)[C:10]([S:29][CH2:30][CH3:31])=[N:9][C:8]=2[C:7]1=[O:32]>C(O)=O>[CH2:30]([S:29][C:10]1[N:11]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:27])([F:28])[F:26])=[CH:19][CH:18]=2)[C:12](=[O:16])[C:13]2[CH2:14][CH2:15][NH:6][C:7](=[O:32])[C:8]=2[N:9]=1)[CH3:31]

Participants

Conditions

Temperature: 100 °C

Procedure

7-(2,4-Dimethoxybenzyl)-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,5,6,7-tetrahydropyrido[3,4-d]pyrimidine-4,8-dione (71 mg) was dissolved in formic acid (3 ml), and the solution was stirred at 100° C. for 1 hr, allowed to be cooled to room temperature, and concentrated under reduced pressure. The residue was subjected to azeotropic distillation with toluene. The obtained white solid was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (38 mg) as a white solid.

Workup

temperatureto be cooled to room temperature
concentrationconcentrated under reduced pressure
distillationThe residue was subjected to azeotropic distillation with toluene
customThe obtained white solid was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record: ord-b37c9c30c8fd4dbd9fe61323d2d6254d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023858B2

Reaction notes

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