Phenylsilane → HCID 59395498, compound

HRID 1097674Notes

Reaction equation

HRID 1097674 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[N:10](CC=C)[C:9]=2[C:8](=[O:18])[N:7]([CH2:19][CH2:20][CH2:21][C:22]#[N:23])[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4].C1([SiH3])C=CC=CC=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>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:18])[N:7]([CH2:19][CH2:20][CH2:21][C:22]#[N:23])[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 12752PhenylsilaneHCID 59395626HCID 59395626, compound

Product 1

HCID 59395498HCID 59395498, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

4-[3-Butyl-8-chloro-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purin-1-yl]butanenitrile (2.1 g, 6 mmol) was stirred in a mixture of nitrogen degassed DCM (20 ml) and AcOH (2 ml). Tetrakis(triphenylphosphine)palladium (675 mg, 0.6 mmol) and phenyl silane (7.4 ml, 60 mmol) were added and the mixture stirred at rt for 2 d. This was then evaporated and the residue triturated with a mixture of diethylether:cyclohexane (1:1) to afford the title compound (1.47 g, 60%) as a white solid.

Workup

  1. customdegassed DCM (20 ml) and AcOH (2 ml)
  2. customThis was then evaporated
  3. customthe residue triturated with a mixture of diethylether:cyclohexane (1:1)

Sources & evidence

ORD record
ord-fccff3e42bfc4efaa2bb43086f31efc8
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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