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

Methanol → HCID 57792030, compound

HRID 421976
Notes
Print preview

Reaction equation

HRID 421976 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13](Cl)[N:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:19](=[O:22])([O-])[OH:20].[Na+].[CH3:24]O.[C]=O>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CN(C)C=O>[C:1]([N:5]1[C:9]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([C:19]([O:20][CH3:24])=[O:22])[N:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 57792028HCID 57792028, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 57792030HCID 57792030, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetate
Catalyst
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.93 g of N-(1-tert-butyl-1H-pyrazol-5-yl)-2-chloro-6-methylpyrimidine -4-amine, 328 mg of palladium acetate, 804 mg of 1,1′-bisdiphenylphosphinoferrocene, 920 mg of sodium hydrogen carbonate, 20 ml of methanol and 20 ml of N,N-dimethylformamide was stirred at 100° C. for 16 hours under 3 atmospheric pressure of carbon monoxide, cooled to room temperature, and then diluted with ethyl acetate. An insoluble matter was filtered off using Celite and the resulting ethyl acetate solution was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated. The residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=7/1 to 0/1) to give the title compound.

Workup

  1. filtrationAn insoluble matter was filtered off
  2. washthe resulting ethyl acetate solution was washed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=7/1 to 0/1)

Sources & evidence

ORD record
ord-32abfa5726ae4214ab0f8062ff04b51e
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101621B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes