Acetyl chloride → 2-Acetamido-5-bromopyrimidine

HRID 1921024Notes

Reaction equation

HRID 1921024 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.N1C(C)=CC=CC=1C.[C:17](Cl)(=[O:19])[CH3:18]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:17](=[O:19])[CH3:18])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 79372,6-LutidineHCID 2313102-Amino-5-bromopyrimidine

Product 1

HCID 225937242-Acetamido-5-bromopyrimidineYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-aminopyrimidine (2.0 g, 11.5 mmole) in CH2Cl2 (75 mL) at RT was added 2,6-lutidine (2.7 mL, 23.0 mmole) followed by acetyl chloride (0.99 g, 12.6 mmole). After stirring for 8 hours, the reaction solution was concentrated under vacuum. The remaining residue was dissolved EtOAc (200 mL), washed with H2O (100 mL) and brine, and dried over Na2SO4. Flash chromatography on silica gel (95:5 CHCl3/MeOH) and drying under high vacuum gave the title compound (1.74 g, 70%) as a yellow solid: MS (ES) m/e 217 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. dissolutionThe remaining residue was dissolved EtOAc (200 mL)
  3. washwashed with H2O (100 mL) and brine
  4. dry with materialdried over Na2SO4
  5. customFlash chromatography on silica gel (95:5 CHCl3/MeOH) and drying under high vacuum

Sources & evidence

ORD record
ord-f83244227ccc45378626a321f932eb2c
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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