Trifluoroacetic acid → 3-chloro-4-hydroxy-2'-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one

HRID 2199522Notes

Reaction equation

HRID 2199522 reaction equation
[Cl:1][C:2]1[C:3](=[O:36])[N:4]([C:19]2[C:24]([CH3:25])=[CH:23][N:22]=[C:21]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([C:32]([OH:35])([CH3:34])[CH3:33])[N:27]=3)[CH:20]=2)[C:5]([CH3:18])=[CH:6][C:7]=1[O:8]CC1C=CC(OC)=CC=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3](=[O:36])[N:4]([C:19]2[C:24]([CH3:25])=[CH:23][N:22]=[C:21]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([C:32]([OH:35])([CH3:33])[CH3:34])[N:27]=3)[CH:20]=2)[C:5]([CH3:18])=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866993073-chloro-2'-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-4-((4-methoxybenzyl)oxy)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one

Product 1

HCID 866993063-chloro-4-hydroxy-2'-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-oneYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-2′-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-4-((4-methoxybenzyl)oxy)-5′,6-dimethyl-2H-[1,4′-bipyridin]-2-one (2.53 g, 5.00 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (1.0 mL). The solution was stirred for several hours at room temperature. The solution was concentrated, diluted with water and extracted several times with ethyl acetate. The combined organic layers were dried (MgSO4), filtered and concentrated to provide 1.7 g of the title compound: MS (M+H) 388.

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with water
  3. extractionextracted several times with ethyl acetate
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec934604618c499ba2eac55f7f066c17
Source dataset
uspto-grants-2016_06
Patent number
US09359300B2

Reaction notes

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