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

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

Participants

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

customCO (g) was bubbled through the solution
customThe solvent was removed in vacuo
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

Linked notes

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