Boron tribromide → (6-Chloro-5-methylpyrimidin-4-yl)methanol

HRID 2401215Notes

Reaction equation

HRID 2401215 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([CH2:9][O:10]C)[N:5]=[CH:4][N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([CH2:9][OH:10])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 143061604-Methoxymethyl-5-methyl-6-chloropyrimidine2×

Product 1

HCID 86762586(6-Chloro-5-methylpyrimidin-4-yl)methanolYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Chloro-5-methyl-6-[(methyloxy)methyl]pyrimidine (Intermediate 49, 2.14 g, 12.40 mmol) was dissolved in DCM (105 ml), cooled in an ice bath and treated with 1M boron tribromide in DCM (13.64 ml, 13.64 mmol). The resulting mixture was stirred for 1 hour, allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched by adding water and diluted with DCM. The DCM layer was separated, dried under magnesium sulfate and evaporated under reduced pressure to give the title compound as a yellow solid (1.70 g) m/z (ES+) 159 (M+1), title compound is 49% pure by LCMS. Also contains (6-bromo-5-methyl-4-pyrimidinyl)methanol, m/z (ES+) 203, 205 (M+1) (49% by LCMS)

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred for 1 hour
  3. customThe reaction was quenched
  4. additionby adding water
  5. additiondiluted with DCM
  6. customThe DCM layer was separated
  7. customdried under magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-01cfe403da97458db54d9d25141f1dbc
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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