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Methanol → Methyl 4,5-Diphenyl-pyrimidine-2-carboxylate

HRID 12572
Notes
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Reaction equation

HRID 12572 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][N:3]=1.[C:20]([O-:23])(=[O:22])C.[Na+].[CH3:25]O>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:8]1([C:6]2[C:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:4][N:3]=[C:2]([C:20]([O:23][CH3:25])=[O:22])[N:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 126742762-Chloro-4,5-diphenylpyrimidine

Product 1

HCID 59338828Methyl 4,5-Diphenyl-pyrimidine-2-carboxylate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
Catalyst
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 2-chloro-4,5-diphenyl-pyrimidine (107, 203 mg, 0.76 mmol) and sodium acetate (188 mg, 2.21 mmol) in MeOH (6 ml) and THF (2 ml) was degassed under argon for 10 min. Pd(OAc)2 (2.1 mg) and DPPF (13 mg) were added and CO (g) was bubbled through the solution. The reaction was heated to 110° C. in a sealed tube for 2 days. The solvent was removed in vacuo and the crude product was purified by column chromatography (10% ethyl acetate in hexane) to get the title compound.

Workup

  1. customCO (g) was bubbled through the solution
  2. customThe solvent was removed in vacuo
  3. customthe crude product was purified by column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9bea9c85f39b4b5ab7219d457a1b1a99
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728014B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes