((Chloromethyl)phenylethyl)-trimethoxysilane → 2-(4-(2-(Trimethoxysilyl)ethyl)benzylthio)pyrimidine

HRID 2103958Notes

Reaction equation

HRID 2103958 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8](O[K])C.ClC[CH:14]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:15][Si:16]([O:21][CH3:22])([O:19][CH3:20])[O:17][CH3:18]>C(O)C>[CH3:22][O:21][Si:16]([O:17][CH3:18])([O:19][CH3:20])[CH2:15][CH2:14][C:23]1[CH:24]=[CH:25][C:26]([CH2:8][S:1][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 53426825((Chloromethyl)phenylethyl)-trimethoxysilaneHCID 178418793HCID 178418793, compoundHCID 178473702HCID 178473702, compound

Product 1

HCID 578047282-(4-(2-(Trimethoxysilyl)ethyl)benzylthio)pyrimidineYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 mmole of 2-mercaptopyrimidine was dissolved in 20 ml ethanol, then 10 mmole EtOK was added, and stirred for 5 minutes. 10 mmole of ((chloromethyl)phenylethyl)trimethoxysilane was added to the solution, and stirred for 6 hours. The white precipitate was removed by filtration, the solvent in the filtrate was removed in vacuum. The obtained viscous liquid was separated with a Si gel column (solvents: 1 ethylacetate/3 hexane). 1H NMR (CD3Cl): δ(ppm) 8.50 (2H, m, Pyr.-H), 7.25 (4H, m, Ar—H), 6.95 (1H, m, Pyr.-H), 4.38 (2H, s —CH2—), 3.54 (9H, s, —CH3), 2.70 (2H, m, —CH2—), 0.99 (2H, m, —CH2—). Yield: 73%.

Workup

  1. stirringstirred for 6 hours
  2. customThe white precipitate was removed by filtration
  3. customthe solvent in the filtrate was removed in vacuum
  4. customThe obtained viscous liquid was separated with a Si gel column (solvents: 1 ethylacetate/3 hexane)

Sources & evidence

ORD record
ord-430082e982d24ab2b5cb9e36cc4e8ab8
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

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