3-Pyridinylboronic acid → Ethyl 2-tert-butyl-4-(pyridin-3-yl)pyrimidine-5-carboxylate

HRID 1930378Notes

Reaction equation

HRID 1930378 reaction equation
[C:1]([C:5]1[N:10]=[C:9](Cl)[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:5]1[N:10]=[C:9]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 24903912Ethyl 2-(tert-butyl)-4-chloropyrimidine-5-carboxylate

Product 1

HCID 68983241Ethyl 2-tert-butyl-4-(pyridin-3-yl)pyrimidine-5-carboxylateYield 28.3%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Using a procedure analogous to Example B41, ethyl 2-tert-butyl-4-chloropyrimidine-5-carboxylate from Example B40 (0.30 g, 1.24 mmol) and pyridin-3-ylboronic acid (1.8 g, 1.48 mmol) in presence of tetrakis(triphenylphosphine)palladium(0) (71 mg, 0.062 mmol) were combined to afford ethyl 2-tert-butyl-4-(pyridin-3-yl)pyrimidine-5-carboxylate (0.10 g, 28% yield).

Sources & evidence

ORD record
ord-e6f128ded30848f2955d736ab7faf0ac
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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