Sodium Hydroxide → 4-(2-(methylthio)pyrimidin-4-yl)pyridin-2(1H)-one

HRID 1774142Notes

Reaction equation

HRID 1774142 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=2)[CH:5]=[CH:4][N:3]=1.[OH-:16].[Na+]>Cl>[CH3:15][S:14][C:10]1[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][NH:3][C:2](=[O:16])[CH:7]=2)[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866966454-(2-Fluoropyridin-4-yl)-2-(methylthio)pyrimidine

Product 1

HCID 717270054-(2-(methylthio)pyrimidin-4-yl)pyridin-2(1H)-oneYield 49%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 4-(2-fluoropyridin-4-yl)-2-(methylthio)pyrimidine (6.83 g, 30.9 mmol) in 2N HCl (100 mL) was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature and placed in an ice bath. The pH was adjusted to about 7 with 2N NaOH (about 100 mL). The resulting solids were collected by filtration, washed with water and dried to give 4-(2-(methylthio)pyrimidin-4-yl)pyridin-2(1H)-one (5.07 g) as a solid. This material was placed in the thimble of a Soxhlet apparatus and was attached to a 1 L flask charged with ethyl acetate (500 mL). The material was continuously extracted for 3 days. The resulting white precipitate from the ethyl acetate layer was collected by filtration (3.3 grams, 49% yield). 1H NMR (400 MHz, (CD3)2SO) δ 11.85 (br, s, 1H), 8.75 (d, J=5.0 Hz, HA), 7.79 (d, J=5.0 Hz, 1H), 7.54 (d, J=7.0 Hz, 1H), 7.13 (s, 1H), 6.86 (d, J=7.0 Hz, 1H), 2.58 (s, 3H); m/z (APCI-pos) M+1=220.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customplaced in an ice bath
  4. filtrationThe resulting solids were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-76a26a232973435496276e35b3f0c87e
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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