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

HRID 576977Notes

Reaction equation

HRID 576977 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8]C)[C:3]=1[CH2:10][S:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH3:19])[N:13]=1.B(Br)(Br)Br.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[CH2:10][S:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH3:19])[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 25134Boron tribromideHCID 178490246HCID 178490246, compound

Product 1

HCID 1784295122-[(2-chloro-6-hydroxyphenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 250 mL round bottom flask, 2-{[(2-chloro-6-methoxyphenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (200 mg, 0.67 mmol) was dissolved in DCM (10 mL). BBr3 (1.42 mL, 1.42 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight. Water (5 mL) was added, followed by Na2SO4 (20 g) and DCM (100 mL) after 5 minutes. The solution was filtered and evaporated. The crude product was purified by column chromatography to provide the title compound as a white solid (180 mg, 95% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.06 (s, 3H), 4.48 (s, 2H), 6.02 (br, 1H), 6.83 (d, 1H), 6.93 (d, 1H), 7.15 (t, 1H), 10.44 (br, 1H); M+ 283.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-8d9c54eac36a44e6ba5efa76362b5597
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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