Acetyl chloride → 2-Acetamido-5-bromopyrimidine

HRID 225896Notes

Reaction equation

HRID 225896 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-0bf2cd4bcef84f4e9784796275e34ef8
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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