HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Barium bromate → 4-(3-Hydroxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

HRID 733190
Notes
Print preview

Reaction equation

HRID 733190 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([S:28](=[O:32])(=[O:31])[NH:29][CH3:30])[CH:19]=2)[N:15]=[C:14]([C:33]#[N:34])[N:13]=1)C1C=CC=CC=1.S([O-])([O-])(=O)=O.[Ce+3].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[Ce+3].Br([O-])(=O)=O.[Ba+2].Br([O-])(=O)=O>C(#N)C.O>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:21]=[C:20]([S:28](=[O:32])(=[O:31])[NH:29][CH3:30])[CH:19]=2)[N:15]=[C:14]([C:33]#[N:34])[N:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 61706Barium bromateHCID 159674Cerous sulfateHCID 690470054-(3-Benzyloxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

Product 1

HCID 578391264-(3-Hydroxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrileYield 27.2%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(3-benzyloxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (14.4 mg) in acetonitrile (700 μL) and water (300 μL) was added cerium sulphate (3 mg) and barium bromate (6 mg). The mixture was heated to reflux overnight then filtered through a sinter glass funnel, the residue washed with DCM (10 mL). The filtrate was washed with saturated sodium thiosulphate (10 mL) organics separated, dried over sodium sulphate, filtered, and solvent was removed under reduced pressure to yield crude product. Purification by preparative-H PLC afforded 4-(3-hydroxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (3.2 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. filtrationthen filtered through a sinter glass funnel
  4. washthe residue washed with DCM (10 mL)
  5. washThe filtrate was washed with saturated sodium thiosulphate (10 mL) organics separated
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customsolvent was removed under reduced pressure
  9. customto yield crude product
  10. customPurification by preparative-H PLC

Sources & evidence

ORD record
ord-5b4686ede87146bf8431d57f4bb1ca83
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07589095B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes