Water → HCID 68015339, compound

HRID 570739Notes

Reaction equation

HRID 570739 reaction equation
[CH2:1]([S:3][C:4]1[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=2)[C:6](=[O:15])[C:7]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[C:8]=2[N:9]=1)[CH3:2].[H-].[Na+].I[CH3:31].O>CN(C)C=O>[CH2:1]([S:3][C:4]1[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:26])([F:27])[F:25])=[CH:18][CH:17]=2)[C:6](=[O:15])[C:7]2[CH:13]=[CH:12][N:11]([CH3:31])[C:10](=[O:14])[C:8]=2[N:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68015322HCID 68015322, compound

Product 1

HCID 68015339HCID 68015339, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dione (40 mg) in N,N-dimethylformamide (5 ml) was added sodium hydride (60% in oil, 193 mg) at room temperature, and the mixture was stirred for 10 min. To the reaction mixture was added iodomethane (0.009 ml), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added water, and the precipitate was collected by filtration. The obtained solid was suspended in toluene, and the suspension was concentrated under reduced pressure. The residue was recrystallized from a mixed solvent of hexane/ethyl acetate/methanol to give the title compound (33 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. filtrationthe precipitate was collected by filtration
  3. concentrationthe suspension was concentrated under reduced pressure
  4. customThe residue was recrystallized from a mixed solvent of hexane/ethyl acetate/methanol

Sources & evidence

ORD record
ord-36e6933b17fc478bbed02fc735f50246
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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