Hydrochloric Acid → 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

HRID 570728Notes

Reaction equation

HRID 570728 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:4]=1[CH2:5][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])[NH:9][C:8]=2[C:7]1=[O:30].[OH-].[Na+].I[CH2:40][CH3:41].Cl>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:4]=1[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12](=[O:16])[N:11]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:21][CH:22]=3)[C:10]([S:29][CH2:40][CH3:41])=[N:9][C:8]=2[C:7]1=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 866853867-(2,4-Dimethoxybenzyl)-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,3,5,6,7-hexahydropyrido[3,4-d]pyrimidine-4,8-dione

Product 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2,4-dimethoxybenzyl)-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,3,5,6,7-hexahydropyrido[3,4-d]pyrimidine-4,8-dione (68 mg) in N,N-dimethylformamide (2 ml) were added 1M aqueous sodium hydroxide solution (140 μl) and iodoethane (11 μl), and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into 0.5M hydrochloric acid (4 ml), and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the colorless title compound (72 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-974fffb603c1417596d87414c2f69b21
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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