Pyridine → tert-Butyl 2-chloropyrimidine-4-carboxylate

HRID 509288Notes

Reaction equation

HRID 509288 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[C:17]1([CH3:27])[CH:22]=CC(S(Cl)(=O)=O)=C[CH:18]=1.C([O-])(O)=O.[Na+]>CC(O)(C)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][C:17]([CH3:27])([CH3:22])[CH3:18])=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 221357512-Chloropyrimidine-4-carboxylic acid

Product 1

HCID 57063961tert-Butyl 2-chloropyrimidine-4-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-Chloropyrimidine-4-carboxylic acid (500 mg, 3.154 mmol) was suspended in 2-methylpropan-2-ol (20 ml), followed by addition of pyridine (3 ml) and p-toluenesulfonyl chloride (1.2 g, 6.308 mmol), and then resulting mixture was stirred at room temperature under nitrogen stream for 4 hours. The resulting reaction liquid was neutralized by slow addition of a saturated aqueous NaHCO3 solution, and then concentrated under reduced pressure, followed by addition of distilled water (5 ml). The precipitated solid was filtered, followed by vacuum drying, to obtain 420 mg of pale yellow solid (62%).

Workup

  1. customresulting mixture
  2. customThe resulting reaction liquid
  3. concentrationconcentrated under reduced pressure
  4. additionfollowed by addition of distilled water (5 ml)
  5. filtrationThe precipitated solid was filtered
  6. customdrying

Sources & evidence

ORD record
ord-7a9bd729606d425ea79024f459a132e1
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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