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

HRID 629966Notes

Reaction equation

HRID 629966 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-5070139666ae4cf3a303a6f8cc65d1dd
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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