Carbon Tetrachloride → HCID 68801608, compound

HRID 2099571Notes

Reaction equation

HRID 2099571 reaction equation
O[CH:2]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:39]>C(Cl)Cl>[Cl:39][CH:2]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 68801860HCID 68801860, compound

Product 1

HCID 68801608HCID 68801608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-{hydroxy[2-(methylthio)pyrimidin-4-yl]methyl}benzonitrile (1.65 g, 6.41 mmol) in CCl4 (10 mL) and CH2Cl2(10 mL) was added triphenylphophine (2.36 g, 8.98 mmol) and stirred for 4 h. The mixture was concentrated and the residue was purified by silica gel chromatography (20% EtOAc in hexane) to give 3-{chloro[2-(methylthio)pyrimidin-4-yl]methyl}benzonitrile. 1H-NMR (500 MHz, CDCl3) δ 8.58 (d, 1H, J=5.1), 7.79 (s, 1H), 7.70 (d, 1H, J=8.1), 7.62 (d, 1H, J=7.8), 7.49 (t, 1H, J=7.8), 7.25 (d, 1H, J=4.9), 5.92 (s, 1H), 2.51 (s, 3H). LRMS m/z (M+H) Calcd: 276.8, found: 276.0.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-c20f014a640b4e228fb1d5efafef0bb6
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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