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

HRID 576928Notes

Reaction equation

HRID 576928 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[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]=[CH:6][C:7]([O:9][CH3:10])=[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 124845332-(Bromomethyl)-1-chloro-4-methoxybenzeneHCID 178429541HCID 178429541, compound

Product 1

HCID 1784907342-[(2-chloro-5-methoxyphenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-oneYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the 2-(bromomethyl)-1-chloro-4-methoxybenzene (3.79 g, 16.09 mmol) in anhydrous ethanol (30 mL) at room temperature, 6-methyl-2-sulfanylpyrimidin-4-ol (2.28 g, 16.09 mmol) was added. Triethylamine (1.79 g, 17.7 mmol) was then added. The reaction mixture was stirred overnight at room temperature. The reaction progress was monitored by LCMS. The solvent was evaporated, and the crude residue was suspended in water and sonicated. The white precipitated product was filtered off and washed with water, ether, and ethyl acetate to provide the 2-{[(2-chloro-5-methoxyphenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid (4.05 g, 85% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 3.71 (s, 3H), 4.39 (s, 2H), 5.99 (bs, 1H), 6.88 (d, J=8.9 Hz, 1H), 7.19 (s, 1H), 7.38 (d, J=8.9 Hz, 1H).

Workup

  1. customThe solvent was evaporated
  2. customsonicated
  3. filtrationThe white precipitated product was filtered off
  4. washwashed with water, ether, and ethyl acetate

Sources & evidence

ORD record
ord-7ab8fa073708462d9c471d6bf9eac534
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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