Boron tribromide → HCID 178429482, compound

HRID 629971Notes

Reaction equation

HRID 629971 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][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>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][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

4

Reactant 2

HCID 25134Boron tribromideHCID 1784907342-[(2-chloro-5-methoxyphenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

Product 1

HCID 178429482HCID 178429482, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the 2-{[(2-chloro-5-methoxyphenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (1.0 g, 3.36 mmol) compound in anhydrous dichloromethane at 0° C., 1 M solution of boron tribromide (0.844 g, 3.36 mmol) was added. The reaction mixture was stirred at room temperature overnight. Then, the reaction mixture was quenched with sodium bicarbonate solution and the solid was filtered. The crude solid was purified by using dichloromethane and methanol (1:10) to provide the product 2-{[(2-chloro-5-hydroxyphenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid (0.62 g, 65% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 4.34 (s, 2H), 5.98 (bs, 1H), 6.66 (d, J=8.8 Hz, 1H), 6.97 (s, 1H), 7.20 (d, J=8.8 Hz, 1H); M+283.06.

Workup

  1. customThen, the reaction mixture was quenched with sodium bicarbonate solution
  2. filtrationthe solid was filtered
  3. customThe crude solid was purified

Sources & evidence

ORD record
ord-9041fff1ca6e45239b19dd94fb530c18
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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