4-((Tert-butyldimethylsilyl)oxy)aniline → N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-2-ethoxypyrimidin-5-amine

HRID 515920Notes

Reaction equation

HRID 515920 reaction equation
[Si:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:17]1[CH:18]=[N:19][C:20]([O:23][CH2:24][CH3:25])=[N:21][CH:22]=1>O1CCCC1>[Si:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:17]2[CH:18]=[N:19][C:20]([O:23][CH2:24][CH3:25])=[N:21][CH:22]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 117155534-((Tert-butyldimethylsilyl)oxy)anilineHCID 164271415-Bromo-2-ethoxypyrimidine

Product 1

HCID 131733321N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-2-ethoxypyrimidin-5-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[tert-Butyl(dimethyl)silyl]oxyaniline (1.8 g, 8 mmol) and 5-bromo-2-ethoxy-pyrimidine (1.6 g, 8 mmol) dissolved in anhydrous tetrahydrofuran (30 mL) are stirred for 1 hour at ambient temperature in the presence of sodium tert-butylate (4 mL, 2M solution in THF) and chloro(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)-phenyl]palladium(II) (111 mg, 0.16 mmol). The reaction mixture is filtered over Celite and then evaporated to dryness. The residue is triturated in heptane to obtain the expected compound after filtration.

Workup

  1. filtrationThe reaction mixture is filtered over Celite
  2. customevaporated to dryness
  3. customThe residue is triturated in heptane

Sources & evidence

ORD record
ord-92a797c862764ca2b09f119b1679d126
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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