Triethylamine → 2-[(2-chloro-5-nitrophenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

HRID 576924Notes

Reaction equation

HRID 576924 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[Cl:12].[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.C(N(CC)CC)C>C(O)C>[Cl:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][S:20][C:18]1[N:17]=[C:16]([OH:21])[CH:15]=[C:14]([CH3:13])[N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27640322-(Bromomethyl)-1-chloro-4-nitrobenzeneHCID 178429541HCID 178429541, compound

Product 1

HCID 1784294812-[(2-chloro-5-nitrophenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-oneYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(bromomethyl)-1-chloro-4-nitrobenzene (1.0 g, 4.0 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (512 mg, 3.6 mmol), and triethylamine (560 μL, 4.0 mmol) in absolute ethanol (20 mL) was stirred at room temperature overnight. The product was recovered by filtration, washed with EtOH (2×15 mL) and diethyl ether (3×25 mL), and dried in vacuo, affording the title compound (1.0 g, 90% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.26 (s, 3H), 4.53 (s, 2H), 6.00 (s (br), 1H), 7.78 (d, 1H, J=8.8 Hz), 8.15 (dd, 1H, J=2.9 Hz, 8.8 Hz), 8.59 (d, 1H, J=2.7 Hz); M+ 312.

Workup

  1. filtrationThe product was recovered by filtration
  2. washwashed with EtOH (2×15 mL) and diethyl ether (3×25 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ce2168ad01ce49f8878bd6df9d1e9076
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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