Triethylamine → 3,6-Dimethyl-2-{[(2,3,6-trichlorophenyl)methyl]sulfanyl}-3,4-dihydro-pyrimidin-4-one

HRID 576919Notes

Reaction equation

HRID 576919 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl:9])=[C:7]([Cl:10])[CH:6]=[CH:5][C:4]=1[Cl:11].[CH3:12][N:13]1[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[N:15]=[C:14]1[SH:21].C(N(CC)CC)C>C(O)C>[CH3:12][N:13]1[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[N:15]=[C:14]1[S:21][CH2:2][C:3]1[C:4]([Cl:11])=[CH:5][CH:6]=[C:7]([Cl:10])[C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 786622-(Bromomethyl)-1,3,4-trichlorobenzeneHCID 178429350HCID 178429350, compound

Product 1

HCID 595893973,6-Dimethyl-2-{[(2,3,6-trichlorophenyl)methyl]sulfanyl}-3,4-dihydro-pyrimidin-4-oneYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(bromomethyl)-1,3,4-trichlorobenzene (576 mg, 2.1 mmol), 3,6-dimethyl-2-sulfanyl-3,4-dihydropyrimidin-4-one (300 mg, 1.9 mmol), and triethylamine (280 μL, 2.0 mmol) in absolute ethanol (10 mL) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure. The solid product was suspended in water (30 mL). The solid material was recovered by filtration, washed with water (2×10 mL) and hexanes (2×20 mL), and dried in vacuo, affording the title compound (475 mg, 72% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 3.31 (s, 3H), 4.77 (s, 2H), 6.08 (s, 1H), 7.57 (d, 1H, J=8.8 Hz), 7.68 (d, 1H, J=8.8 Hz); M+ 350; HPLC purity: 95.8%.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationThe solid material was recovered by filtration
  3. washwashed with water (2×10 mL) and hexanes (2×20 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b14272c636124b75ae4b451defa9fb28
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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