Cesium carbonate → 2-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-({[2-oxo-1-(3-pyridinylmethyl)-1,2-dihydro-4-pyrimidinyl]oxy}methyl)benzonitrile

HRID 536182Notes

Reaction equation

HRID 536182 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[NH:20][C:21](=[O:25])[N:22]=[CH:23][CH:24]=3)=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].Cl.ClC[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1.[C:39]([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][N:22]([CH2:39][C:36]4[CH:35]=[N:34][CH:33]=[CH:38][CH:37]=4)[C:21](=[O:25])[N:20]=3)=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:26]([F:27])([F:29])[F:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochlorideHCID 573831812-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-{[(2-oxo-1,2-dihydro-4-pyrimidinyl)oxy]methyl}benzonitrile

Product 1

HCID 573790142-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-({[2-oxo-1-(3-pyridinylmethyl)-1,2-dihydro-4-pyrimidinyl]oxy}methyl)benzonitrileYield 8.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-{[(2-oxo-2,3-dihydro-4-pyrimidinyl)oxy]methyl}benzonitrile (100 mg, 0.237 mmol), 2-(chloromethyl)pyridine hydrochloride (58.3 mg, 0.356 mmol) and Cs2CO3 (464 mg, 1.42 mmol) in anhydrous N,N-dimethylformamide (10 mL) was sealed in a microwave vial, then irradiated with a microwave at 110° C. for 2 h and filtered. Purification via mass-directed autopreparation afforded the title product (10 mg). LC-MS (ESI): m/z 513 [M+H]+; 4.12 min (ret time).

Workup

  1. customwas sealed in a microwave vial
  2. customirradiated with a microwave at 110° C. for 2 h
  3. filtrationfiltered
  4. customPurification via mass-directed autopreparation

Sources & evidence

ORD record
ord-1deb4f4243b4460faa535ccb8fed6fef
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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