Diethyl Ether → 4-Methyl-2-{[(2,3,6-trichlorophenyl)methyl]sulfanyl}pyrimidine

HRID 576932Notes

Reaction equation

HRID 576932 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([SH:9])[N:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[C:23]([Cl:24])=[C:22]([Cl:25])[CH:21]=[CH:20][C:19]=1[Cl:26].C(OCC)C>CN(C=O)C>[CH3:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([S:9][CH2:17][C:18]2[C:19]([Cl:26])=[CH:20][CH:21]=[C:22]([Cl:25])[C:23]=2[Cl:24])[N:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 786622-(Bromomethyl)-1,3,4-trichlorobenzeneHCID 1784286872-Mercapto-4-methylpyrimidine hydrochloride

Product 1

HCID 595895074-Methyl-2-{[(2,3,6-trichlorophenyl)methyl]sulfanyl}pyrimidineYield 22.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-methylpyrimidine-2-thiol hydrochloride (200 mg, 1.2 mmol) and potassium carbonate (357 mg, 2.6 mmol) was stirred for 30 minutes in anhydrous DMF (4 mL) at room temperature. Then, 2-(bromomethyl)-1,3,4-trichlorobenzene (345 mg, 1.3 mmol) in anhydrous DMF (1 mL) was added, and the mixture was stirred overnight at room temperature. The solid was removed by filtration and filtrate evaporation. The residue was dissolved in DCM and purified on silica gel using 5% DCM/MeOH to afford, after trituration with diethyl ether, 4-methyl-2-{[(2,3,6-trichlorophenyl)methyl]sulfanyl}pyrimidine as a white solid (88 mg, 22% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.44 (s, 3H), 4.75 (s, 2H), 6.09 (s, 1H), 7.17 (d, J=5.1 Hz, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.67 (d, J=8.7 Hz, 1H), 8.54 (d, J=5.1 Hz, 1H); LRMS (ES+) m/z 319 (100%, M+1), 321 (100%, M+3), 323 (35%, M+5).

Workup

  1. customThe solid was removed by filtration and filtrate evaporation
  2. dissolutionThe residue was dissolved in DCM
  3. custompurified on silica gel using 5% DCM/MeOH
  4. customto afford

Sources & evidence

ORD record
ord-27af6d74fe8c453c9e6693262090e543
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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