Iodine → 2-(4-(tert-Butyldimethylsilyloxy)benzyl)pyrimidine

HRID 2075222Notes

Reaction equation

HRID 2075222 reaction equation
II.Br[CH2:4][C:5]1[CH:18]=[CH:17][C:8]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:7][CH:6]=1.Br[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>CN(C=O)C.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:10]([O:9][C:8]1[CH:17]=[CH:18][C:5]([CH2:4][C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:6][CH:7]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 807IodineHCID 783452-BromopyrimidineHCID 10380115(4-(Bromomethyl)phenoxy)(tert-butyl)dimethylsilaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 584153612-(4-(tert-Butyldimethylsilyloxy)benzyl)pyrimidine

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent2×

Procedure

Zinc (0.33 g, 4.97 mmol) and iodine (0.008 g, 0.033 mmol) were added to an oven-dried flask (25 mL). The mixture was heated under vacuum with a heat gun for 10 min, cooled to RT, placed under argon atmosphere, suspended in 3 mL DMF (dry, degassed by bubbling nitrogen through it for 10 min), and cooled to 0° C. (4-(Bromomethyl)phenoxy)(tertbutyl)dimethylsilane (1.00 g, 3.31 mmol) was added as a solution in 3 mL DMF, the mixture was stirred at 0° C. for 30 min, then room temperature for 30 min. Next, 2-bromopyrimidine (526 mg, 3.31 mmol), Pd2 dba3 (0.091 mg, 0.099 mmol), and S-Phos (0.163 g, 0.40 mmol) were added. The flask was purged with argon and heated for 1 h at 60° C., cooled to RT, filtered through Celite, and concentrated in vacuo. The resulting solid was purified by flash chromatography to give title compound as a light yellow oil. MS (ESI) m/z: Calculated: 300.2; Observed: 301.5 (M++1).

Workup

  1. temperatureThe mixture was heated under vacuum with a heat gun for 10 min
  2. waitroom temperature for 30 min
  3. customThe flask was purged with argon
  4. temperatureheated for 1 h at 60° C.
  5. temperaturecooled to RT
  6. filtrationfiltered through Celite
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was purified by flash chromatography

Sources & evidence

ORD record
ord-fbb6c5c6a37145eaa2373211980eec7a
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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