Boron tribromide → HCID 67419432, compound

HRID 1774419Notes

Reaction equation

HRID 1774419 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([O:16]C)=[CH:10][N:9]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([OH:16])=[CH:10][N:9]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:19])[F:20]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67408142HCID 67408142, compound

Product 1

HCID 67419432HCID 67419432, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 625 mg (1.96 mmol) 2-[4-chloro-3-(trifluoromethyl)phenyl]-5-methoxy-3-methylpyrimidin-4(3H)-one in 25 ml CH2Cl2 was added 5.88 ml (5.88 mmol) of a 1 M solution of BBr3 in CH2Cl2. The reaction mixture was stirred for 1 h, then quenched with 25 ml MeOH, and concentrated in vacuo. Purification by HPLC gave 418 mg (70% yield) of 2-[4-chloro-3-(trifluoromethyl)phenyl]-5-hydroxy-3-methylpyrimidin-4(3H)-one. 1H NMR δ (ppm)(CDC3): 7.86 (1 H, d, J=1.95 Hz), 7.73 (1 H, s), 7.67-7.61 (2 H, m), 3.54 (3 H, s). HRMS (ESI positive) calc (M+H)+=305.0299. Found 305.0300.

Workup

  1. customquenched with 25 ml MeOH
  2. concentrationconcentrated in vacuo
  3. customPurification by HPLC

Sources & evidence

ORD record
ord-1d17e114d68d4627bc9a09edf1f4b6fd
Source dataset
uspto-grants-2016_02
Patent number
US09260413B2

Reaction notes

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