Cesium fluoride → 2-methyl-5-[1-(phenylmethyl)-2,5-dihydro-1H-pyrrol-3-yl]pyrimidine

HRID 1715200Notes

Reaction equation

HRID 1715200 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.[C:9]1([CH2:15][N:16]2[CH2:20][CH:19]=[C:18](B3OC(C)(C)C(C)(C)O3)[CH2:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F-].[Cs+]>C1COCC1.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>[CH3:8][C:5]1[N:4]=[CH:3][C:2]([C:18]2[CH2:17][N:16]([CH2:15][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:20][CH:19]=2)=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 114603191-Benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole2×HCID 143877445-Bromo-2-methylpyrimidine2×

Product 1

HCID 578560242-methyl-5-[1-(phenylmethyl)-2,5-dihydro-1H-pyrrol-3-yl]pyrimidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 178418397HCID 178418397, compoundSolvent

Conditions

Temperature
80 °C

Procedure

The title compound can be prepared through a coupling palladium mediated reaction, e.g. starting from 5-bromo-2-methylpyrimidine and 1-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole. For example, to a solution of 5-bromo-2-methylpyrimidine (1.3 eq.) in THF, 1-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole (1 eq.), tetrakis(triphenylphosphine)palladium(0) (5% mol) and cesium fluoride (4 eq.) may be added at room temperature. The resulting mixture should be stirred at 80° C. for 1.5 hours. After cooling the solvent should be evaporated under reduced pressure and the residue partitioned between dichloromethane and sodium hydroxyde (1M). The organic phase should be evaporated under reduced pressure and the crude product purified by flash chromatography to give the title compound.

Workup

  1. custommay be added at room temperature
  2. temperatureAfter cooling the solvent
  3. customshould be evaporated under reduced pressure
  4. customthe residue partitioned between dichloromethane and sodium hydroxyde (1M)
  5. customThe organic phase should be evaporated under reduced pressure
  6. customthe crude product purified by flash chromatography

Sources & evidence

ORD record
ord-6ad26a735ad14ae591ec8e415f1ae3ed
Source dataset
uspto-grants-2010_09
Patent number
US07799815B2

Reaction notes

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