Ethanol → 2-ethoxy-6-methyl-N-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)pyrimidine-4-carboxamide

HRID 623641Notes

Reaction equation

HRID 623641 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][CH:11]([C:13]2[CH:14]=[N:15][C:16]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[C:17]([CH3:19])[CH:18]=2)[CH3:12])=[O:9])[CH:5]=[C:4]([CH3:26])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:33]([OH:35])[CH3:34]>>[CH2:33]([O:35][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH:11]([C:13]2[CH:14]=[N:15][C:16]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[C:17]([CH3:19])[CH:18]=2)[CH3:12])=[O:9])[CH:5]=[C:4]([CH3:26])[N:3]=1)[CH3:34]

Participants

4

Reactant 3

HCID 702EthanolHCID 10796Cesium carbonateHCID 874272192-chloro-6-methyl-N-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)pyrimidine-4-carboxamide

Product 1

HCID 675098532-ethoxy-6-methyl-N-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)pyrimidine-4-carboxamideYield 41%

Conditions

Temperature
160 °C

Procedure

A mixture of 2-chloro-6-methyl-N-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)pyrimidine-4-carboxamide (40 mg, 0.1 mmol, Step-1 of Example 456, single enantiomer) and cesium carbonate (50 mg, 0.15 mmol) in ethanol (2 mL) is heated by microwave irradiation at 160° C. for 1 hour. After cooled to room temperature, the mixture is concentrated under reduced pressure. The residue is suspended in ethyl acetate and filtered through a short column of amine gel eluting with ethyl acetate. The filtrate is concentrated and then by preparative LC-MS to give 17 mg (41% yield) of the title compound.

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe mixture is concentrated under reduced pressure
  3. filtrationfiltered through a short column of amine gel
  4. washeluting with ethyl acetate
  5. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-02fe15777526422790ec4a7fa35c5a8c
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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