m-Formylbenzonitrile → HCID 68801860, compound

HRID 2099570Notes

Reaction equation

HRID 2099570 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C([Mg]Cl)(C)C.[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])#[N:16]>C1COCC1>[OH:21][CH:20]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1)[C:19]1[CH:18]=[C:17]([CH:24]=[CH:23][CH:22]=1)[C:15]#[N:16]

Participants

5

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 178418918HCID 178418918, compound

Product 1

HCID 68801860HCID 68801860, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 4-iodo-2-(methylthio)pyrimidine (2.52 g, 10 mmol) in THF (50 mL) at 0 ° C. was added i-PrMgCl (5 mL, 2.0 M, 10 mmol) and stirred for 1 h. 3-cyanobenzaldehyde (1.31 g, 10 mmol) was added. The mixture was stirred at 0° C. for 2 h. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography (20-50% EtOAc in hexane) to give 3-{hydroxy[2-(methylthio)pyrimidin-4-yl]methyl}benzonitrile. 1H-NMR (500 MHz, CDCl3) δ 8.46 (d, 1H, J=5.1), 7.72 (s, 1H), 7.65 (d, 1H, J=7.9), 7.61 (d, 1H, J=7.8), 7.48 (t, 1H, J=7.6), 6.84 (d, 1H, J=5.1), 5.69 (d, 1H, J=3.7), 4.58 (d, 1H, J=4.1), 2.60 (s, 3H). LRMS m/z (M+H) Calcd: 258.3, found: 258.1.

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 h
  2. customThe reaction was quenched with saturated aqueous NH4Cl solution
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (20-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-46f2e68ac142471487fa4f6544c690c9
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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