4-Toluenesulfonyl chloride → Tert-butyl 5-bromopyrimidine-2-carboxylate

HRID 1177147Notes

Reaction equation

HRID 1177147 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[C:11]1([CH3:21])[CH:16]=CC(S(Cl)(=O)=O)=C[CH:12]=1>CC(O)(C)C.N1C=CC=CC=1>[C:11]([O:9][C:8]([C:5]1[N:6]=[CH:7][C:2]([Br:1])=[CH:3][N:4]=1)=[O:10])([CH3:21])([CH3:16])[CH3:12]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 164629705-Bromopyrimidine-2-carboxylic acid

Product 1

HCID 59560347Tert-butyl 5-bromopyrimidine-2-carboxylateYield 56.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6386tert-ButanolSolvent

Procedure

A suspension of 5-bromopyrimidine-2-carboxylic acid (690 mg, 3.40 mmol) in 6.8 mL t-BuOH and 1.9 mL pyridine was stirred at room temperature to 50° C. for 1 hr, and cooled to room temperature. 4-Toluenesulfonyl chloride (1.55 g, 8.12 mmol) was added portion wise. The mixture was stirred at room temperature for 1.5 h. The reaction was quenched with saturated aqueous NaHCO3 slowly, extracted with 3×Et2O, dried over Na2SO4, and concentrated. The residue was purified by Biotage column chromatography with 15-25% EtOAc in hexanes to give a yellow solid (497 mg, 56% yield). 1H NMR (400 MHz, CDCl3) δ 8.94 (s, 2 H) 1.64 (s, 9 H).

Workup

  1. stirringThe mixture was stirred at room temperature for 1.5 h
  2. customThe reaction was quenched with saturated aqueous NaHCO3 slowly
  3. extractionextracted with 3×Et2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by Biotage column chromatography with 15-25% EtOAc in hexanes

Sources & evidence

ORD record
ord-41fde06ab9164619a69077e94648eb2e
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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