HCID 86685391, compound → HCID 68015322, compound

HRID 570732Notes

Reaction equation

HRID 570732 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH:15]=[CH: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[CH:14]=[CH:15][NH:6][C:7](=[O:32])[C:8]=2[N:9]=1)[CH3:31]

Participants

3

Reactant 1

HCID 86685391HCID 86685391, compound

Product 1

HCID 68015322HCID 68015322, compoundYield 83.1%

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]-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dione (219 mg) was dissolved in formic acid (5 ml), and the solution was stirred at 100° C. for 3 hr, allowed to be cooled to room temperature, and concentrated under reduced pressure. To the residue was added toluene, and the mixture was again concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and recrystallized from a mixed solvent of ethyl acetate/hexane/methanol to give the title compound (132 mg).

Workup

  1. temperatureto be cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added toluene
  4. concentrationthe mixture was again concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  6. customrecrystallized from a mixed solvent of ethyl acetate/hexane/methanol

Sources & evidence

ORD record
ord-50f540ada3e24b64a63f6a36bdb94f03
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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