2-(Tributylstannyl)pyrimidine → Methyl 5-methoxy-4-methyl-2-(pyrimidin-2-yl)benzoate

HRID 1477744Notes

Reaction equation

HRID 1477744 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.Br[C:21]1[CH:30]=[C:29]([CH3:31])[C:28]([O:32][CH3:33])=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24]>COCCOC.CCOC(C)=O.O.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>[CH3:33][O:32][C:28]1[C:29]([CH3:31])=[CH:30][C:21]([C:6]2[N:7]=[CH:8][CH:9]=[CH:10][N:11]=2)=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

7

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 20428669Methyl 2-bromo-5-methoxy-4-methylbenzoate

Product 1

HCID 90422098Methyl 5-methoxy-4-methyl-2-(pyrimidin-2-yl)benzoate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pd(PPh3)4 (416 mg, 0.36 mmol) was added to a rt solution of 2-tributylstannylpyrimidine (1.40 g, 3.6 mmol) and methyl 2-bromo-5-methoxy-4-methylbenzoate (1.03 g, 3.96 mmol) in degassed DME (7 mL) and the resulting mixture was irradiated in the microwave at 160° C. for 1 h. To the rxn mixture was added Pd(PPh3)4 (315 mg, 0.27 mmol) and irradiation was continued at 160° C. for another 2 h. The rxn mixture was diluted with EtOAc and H2O, filtered over celite, the org. layer was separated and the aq. layer was re-extracted with EtOAc. The combined org. extracts were dried (MgSO4), filtered, concentrated in vacuo and purified by FC (Biotage SP1: EtOAc/hex 1:9 to 3:7) to yield methyl 5-methoxy-4-methyl-2-(pyrimidin-2-yl)benzoate as a brown solid which was used without further purification. LC-MS A: tR=0.75 min, [M+H]+=258.99.

Workup

  1. customthe resulting mixture was irradiated in the microwave at 160° C. for 1 h
  2. additionTo the rxn mixture was added
  3. filtrationfiltered over celite
  4. customlayer was separated
  5. extractionthe aq. layer was re-extracted with EtOAc
  6. dry with materialextracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified by FC (Biotage SP1: EtOAc/hex 1:9 to 3:7)

Sources & evidence

ORD record
ord-ddf2d41b7e184685a883a149da3e8ad6
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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