4-Vinylbenzene chloride → 2-(4-Vinylbenzylthio)pyrimidine

HRID 2103947Notes

Reaction equation

HRID 2103947 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8](O[K])C.[Cl-].[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:14]>C(O)C>[CH:13]([C:15]1[CH:20]=[CH:19][C:18]([CH2:8][S:1][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:17][CH:16]=1)=[CH2:14]

Participants

5

Reactant 3

HCID 180086044-Vinylbenzene chlorideHCID 178418793HCID 178418793, compoundHCID 178473702HCID 178473702, compound

Product 1

HCID 578047112-(4-Vinylbenzylthio)pyrimidineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 mmole of 2-mercaptopyrimidine was dissolved in 20 ml of ethanol in stirring. 10 mole of EtOK was added to the solution, stirred for 5 minutes. Then, 10 mmole of 4-vinylbenzene chloride was added, and stirred overnight. The white precipitate was removed by filtration, the solvent in the filtrate was removed in vacuum. The obtained liquid was separated with a Si gel column (solvents: 1 ethylacetate/3 hexane). 2.1 g product was obtained. Yield: 92%. 1H NMR (CD3Cl): 8.51 (2H, d, JH-H=4.60), 7.38 (4H, m), 6.94 (1H, t, JH-H=4.60), 6.68 (1H, m), 5.70 (1H, d, JH-H=17.58), 5.21 (1H, d, JH-H=10.95), 4.40 (2H, s).

Workup

  1. stirringstirred for 5 minutes
  2. stirringstirred overnight
  3. customThe white precipitate was removed by filtration
  4. customthe solvent in the filtrate was removed in vacuum
  5. customThe obtained liquid was separated with a Si gel column (solvents: 1 ethylacetate/3 hexane)

Sources & evidence

ORD record
ord-0da389d655244183be6d40b1b82a0718
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

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