Potassium Carbonate → HCID 178429462, compound

HRID 577129Notes

Reaction equation

HRID 577129 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:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]2=[N:20][C:19]=1[Cl:27]>CN(C=O)C>[Cl:27][C:19]1[N:20]=[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]2[C:18]=1[CH2:17][S:8][C:6]1[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59589418HCID 59589418, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429462HCID 178429462, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (600 mg, 4.2 mmol) was dissolved in anhydrous DMF (20 mL), and then potassium carbonate (1.75 g, 12.7 mmol) and 3-(bromomethyl)-2-chloroimidazo[1,2-a]pyridine (5.5 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 0-12% DCM/MeOH to afford the title compound (165 mg, 15% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 4.85 (s, 2H), 6.03 (bs, 1H), 7.10 (t, J=6.7 Hz, 1H), 7.39 (t, J=7.0 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 8.59 (d, J=6.8 Hz, 1H); LRMS (ES+) m/z 307 (85%, M+1).

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 0-12% DCM/MeOH

Sources & evidence

ORD record
ord-4d0588100dc647959b1fde0442f801f0
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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