3-Nitrophenylboronic Acid → 2-Chloro-4-(3-nitrophenyl)pyrimidine

HRID 14732

Reaction equation

HRID 14732 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)([O-:11])=[O:10]>>[Cl:1][C:2]1[N:7]=[C:6]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:9]([O-:11])=[O:10])[CH:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 775312,4-Dichloropyrimidine

Product 1

HCID 249018872-Chloro-4-(3-nitrophenyl)pyrimidineYield 60%

Procedure

2,4 dichloropyrimidine was coupled to 3-nitrophenyl boronic acid following procedure A. The workup and purification protocol was modified as follows: The THF was removed from the reaction mixture by rotary evaporation and the residue taken up in ethyl acetate. The solution was washed with water followed by sat. NaCl and the organic layer concentrated by rotary evaporation until the product started to precipitate, at which point the flask was placed in an ice bath for two hours. The product was collected by filtration in a Buchner funnel. The yield was 60%. Product was >95% pure by LC-MS and showed the expected M+H+ of 236.

Workup

  1. customThe workup and purification protocol
  2. customThe THF was removed from the reaction mixture by rotary evaporation
  3. washThe solution was washed with water
  4. concentrationthe organic layer concentrated by rotary evaporation until the product
  5. customto precipitate, at which point the flask
  6. filtrationThe product was collected by filtration in a Buchner funnel

Sources & evidence

ORD record
ord-93733660cfa54bae8dc0899cff879376
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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