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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 570729
Notes
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Reaction equation

HRID 570729 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 866853887-(2,4-Dimethoxybenzyl)-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,5,6,7-tetrahydropyrido[3,4-d]pyrimidine-4,8-dione

Product 1

HCID 680153252-(Ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,5,6,7-tetrahydropyrido[3,4-d]pyrimidine-4,8-dioneYield 73.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

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

  1. temperatureto be cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. distillationThe residue was subjected to azeotropic distillation with toluene
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes