Potassium Carbonate → HCID 178437620, compound

HRID 630196Notes

Reaction equation

HRID 630196 reaction equation
[SH:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]1[C:22]([CH2:28][CH3:29])=[N:23][CH:24]=[CH:25][C:26]=1[Cl:27]>CN(C=O)C>[Cl:27][C:26]1[CH:25]=[CH:24][N:23]=[C:22]([CH2:28][CH3:29])[C:21]=1[CH2:20][S:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]([F:12])([F:10])[F:11])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 595895013-(Bromomethyl)-4-chloro-2-ethylpyridineHCID 178516148HCID 178516148, compound

Product 1

HCID 178437620HCID 178437620, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (884 mg, 4.5 mmol) was dissolved in anhydrous DMF (30 mL), and then potassium carbonate (1.87 g, 13.5 mmol) and 3-(bromomethyl)-4-chloro-2-ethylpyridine (5.4 mmol) in DMF (10 mL) were added. The mixture was stirred overnight at room temperature. The solid was removed by filtration and washed with methanol, and the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 3-10% DCM/MeOH to afford 2-{[(4-chloro-2-ethylpyridin-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (391 mg, 25% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 1.19 (t, J=7.4 Hz, 3H), 2.93 (q, J=7.4 Hz, 2H), 4.66 (s, 2H), 6.69 (s, 1H), 7.43 (d, J=5.3 Hz, 1H), 8.40 (d, J=5.3 Hz, 1H).

Workup

  1. customThe solid was removed by filtration
  2. washwashed with methanol
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in DCM/MeOH
  5. custompurified on silica gel using 3-10% DCM/MeOH

Sources & evidence

ORD record
ord-465c7a77f38249c9b188d2bec83c3d1e
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…