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

HRID 576913Notes

Reaction equation

HRID 576913 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[Cl:11].[CH3:12][C:13]1[N:18]=[C:17]([SH:19])[N:16]=[C:15]([OH:20])[CH:14]=1.C(N(CC)CC)C>C(O)C>[Cl:11][C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[CH2:2][S:19][C:17]1[N:16]=[C:15]([OH:20])[CH:14]=[C:13]([CH3:12])[N:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 223274281-(Bromomethyl)-2-chloro-4-methoxybenzeneHCID 178429541HCID 178429541, compound

Product 1

HCID 1784917022-[(2-chloro-4-methoxyphenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-oneYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(bromomethyl)-2-chloro-4-methoxybenzene (1.0 g, 4.2 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (550 mg, 3.9 mmol), and triethylamine (585 μL, 4.2 mmol) in absolute ethanol (20 mL) was stirred at room temperature overnight. The product was recovered by filtration, washed with water (2×20 mL) and diethyl ether (2×20 mL), and dried in vacuo, affording the title compound (929 mg, 81% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.07 (s, 3H), 3.76 (s, 3H), 4.41 (s, 2H), 6.00 (s (br), 1H), 6.89 (dd, 1H, J=2.5 Hz, 8.6 Hz), 7.07 (d, 1H, J=8.6 Hz), 7.52 (d, 1H, J=8.6 Hz); M+ 297.

Workup

  1. filtrationThe product was recovered by filtration
  2. washwashed with water (2×20 mL) and diethyl ether (2×20 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-9a65e7bda47145e0ad73b01b288cb22e
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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