(Diethylamino)sulfur trifluoride → 2-Chloro-4-(1-fluoroethyl)pyrimidine

HRID 410433Notes

Reaction equation

HRID 410433 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8](O)[CH3:9])[CH:5]=[CH:4][N:3]=1.C(N(S(F)(F)[F:17])CC)C>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([F:17])[CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 772310661-(2-Chloropyrimidin-4-yl)ethanol

Product 1

HCID 866582372-Chloro-4-(1-fluoroethyl)pyrimidineYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(2-chloropyrimidin-4-yl)ethanol (150 mg, 0.950 mmol) in dichloromethane (3 mL) at 0° C. was added diethylaminosulfur trifluoride (183 mg, 1.14 mmol) dropwise and stirred for 3 hr. The solution was diluted with dichloromethane, washed with saturated aqueous NaHCO3, dried with MgSO4, and concentrated to dryness. Purification on silica gel by flash chromatography (0-50% EtOAc/hexanes) afforded 2-chloro-4-(1-fluoroethyl)pyrimidine (75 mg, 0.467 mmol, 49% yield) as a yellow oil. MS ESI: [M+H]+ m/z 161.0. 1H NMR (500 MHz, CDCl3) δ 8.67 (d, J=4.2, 1H), 7.46 (d, J=4.2, 1H), 5.58 (dq, J=6.7, 48, 1H), 1.74-1.57 (m, 3H).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated to dryness
  4. customPurification on silica gel by flash chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-28e7fc473eff4192977d310059266b77
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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