Potassium Carbonate → HCID 178429487, compound

HRID 630081Notes

Reaction equation

HRID 630081 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[N:19]=[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]2[CH:26]=1>CN(C=O)C>[N:19]1[C:18]([CH2:17][S:8][C:6]2[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=2)=[CH:26][N:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4318932-(bromomethyl)imidazo[1,2-a]pyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429487HCID 178429487, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (638 mg, 4.5 mmol) was dissolved in anhydrous DMF (20 mL), then potassium carbonate (1.86 g, 13.5 mmol) and 2-(bromomethyl)imidazo[1,2-a]pyridine (1.42 g, 6.7 mmol) were added. The mixture was stirred overnight at room temperature. The solid was removed by filtration and washed with methanol, where the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 12% DCM/MeOH to afford 2-({imidazo[1,2-a]pyridin-2-ylmethyl}sulfanyl)-6-methylpyrimidin-4-ol as a white solid (631 mg, 52% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.46 (s, 2H), 5.99 (bs, 1H), 6.84 (dt, J=1.7 Hz, J=6.7 Hz, 1H), 7.17-7.22 (m, 1H), 7.45 (dd, J=9.0 Hz, J=0.8 Hz, 1H), 7.86 (s, 1H), 8.46-8.49 (m, 1H); LRMS (ES+) m/z 273 (60%, M+1).

Workup

  1. customThe solid was removed by filtration
  2. washwashed with methanol, where the filtrate
  3. customwas evaporated
  4. dissolutionThe residue was dissolved in DCM/MeOH
  5. custompurified on silica gel using 12% DCM/MeOH

Sources & evidence

ORD record
ord-3bd0c143f0bc4329b3c143b2da5e5b80
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…