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

HRID 629961Notes

Reaction equation

HRID 629961 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-c84ef35aeb3d49af89cda9fe642172df
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…