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Water → HCID 86685359, compound

HRID 570696
Notes
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Reaction equation

HRID 570696 reaction equation
[H-].[Na+].[CH3:3][S:4][CH2:5][CH2:6][CH2:7][OH:8].C(S[C:13]1[N:14]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[CH:27][CH:26]=2)[C:15](=[O:24])[C:16]2[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:17]=2[N:18]=1)CC.O>O1CCCC1>[CH3:3][S:4][CH2:5][CH2:6][CH2:7][O:8][C:13]1[N:14]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[CH:29][CH:30]=2)[C:15](=[O:24])[C:16]2[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:17]=2[N:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 104483-(Methylthio)-1-propanolHCID 24758Sodium hydrideHCID 866853582-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Product 1

HCID 86685359HCID 86685359, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a suspension of sodium hydride (60% in oil, 48 mg) in tetrahydrofuran (5 ml) was added 3-(methylsulfanyl)propan-1-ol (0.206 ml) at room temperature, and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added 2-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (165 mg), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (acetic acid ethyl/hexane) to give the title compound (96 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (acetic acid ethyl/hexane)

Sources & evidence

ORD record
ord-19213e89307746a7a8aae64dc4b484dc
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023858B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes