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

Potassium Carbonate → 3-[{2-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)-4-fluorophenylamino]-1-oxopropyl}amino]propionic acid methyl ester

HRID 215910
Notes
Print preview

Reaction equation

HRID 215910 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][NH:6][C:7](=[O:21])[CH:8](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:9].[CH3:23][N:24]1[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][C:27](=[O:34])[N:26]([C:35]2[CH:40]=[C:39]([NH2:41])[C:38]([Cl:42])=[CH:37][C:36]=2[F:43])[C:25]1=[O:44].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][NH:6][C:7](=[O:21])[CH:8]([NH:41][C:39]1[CH:40]=[C:35]([N:26]2[C:27](=[O:34])[CH:28]=[C:29]([C:30]([F:32])([F:33])[F:31])[N:24]([CH3:23])[C:25]2=[O:44])[C:36]([F:43])=[CH:37][C:38]=1[Cl:42])[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 186192573-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneHCID 866574693-[2-(Toluene-4-sulfonyloxy)-propionylamino]propionic acid methyl ester

Product 1

HCID 672957193-[{2-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)-4-fluorophenylamino]-1-oxopropyl}amino]propionic acid methyl esterYield 38.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[2-(Toluene-4-sulfonyloxy)-propionylamino]propionic acid methyl ester (307 mg) was dissolved in acetonitrile (5 mL). After addition of 1-methyl-3-(5-amino-4-chloro-2-fluorophenyl)-6-trifluoromethyl-1H-pyrimidin-2,4-dione (300 mg) and potassium carbonate (135 mg), the reaction mixture was heated for 6 hours under reflux without cooling. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL). Thus obtained organic layer was dried with magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography to give the target compound (170 mg).

Workup

  1. temperaturethe reaction mixture was heated for 6 hours
  2. temperatureunder reflux
  3. temperaturewithout cooling
  4. washwashed with water (50 mL)
  5. dry with materialThus obtained organic layer was dried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-91a31c9c11284ce29c62dc4c74203fba
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193198B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes