Potassium Carbonate → HCID 178429491, compound

HRID 630263Notes

Reaction equation

HRID 630263 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[CH:27]=[N:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:17][C:18]2[CH:27]=[N:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[N:5]=[C:4]([OH:9])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 52877592-(Bromomethyl)quinoxalineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429491HCID 178429491, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (245 mg, 1.7 mmol) was dissolved in anhydrous DMF (10 mL), and then were added potassium carbonate (357 mg, 2.6 mmol) and 2-(bromomethyl)quinoxaline (500 mg, 2.2 mmol) in anhydrous DMF (5 mL). The mixture was stirred over a weekend at room temperature. The solvent was removed by evaporation, and the residue was dissolved in DCM and purified on silica gel using 10% DCM/MeOH to afford 6-methyl-2-[(quinoxalin-2-ylmethyl)sulfanyl]pyrimidin-4-ol (363 mg, 57% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.17 (s, 3H), 4.72 (s, 2H), 6.01 (bs, 1H), 7.81-7.88 (m, 2H), 8.03-8.11 (m, 2H), 9.10 (s, 1H); LRMS (ES+) m/z 285 (100%, M+1).

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in DCM
  3. custompurified on silica gel using 10% DCM/MeOH

Sources & evidence

ORD record
ord-275a140a3a4b44d5a9e3e61dab364174
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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