Potassium Carbonate → HCID 178436795, compound

HRID 577151Notes

Reaction equation

HRID 577151 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[C:19]([CH2:26][CH3:27])=[N:20][CH:21]=[CH:22][C:23]=1[CH2:24][CH3:25]>CN(C=O)C>[CH2:26]([C: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)=[C:23]([CH2:24][CH3:25])[CH:22]=[CH:21][N:20]=1)[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 595893693-(Bromomethyl)-2,4-diethylpyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178436795HCID 178436795, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (839 mg, 5.9 mmol) was dissolved in anhydrous DMF (30 mL), and then potassium carbonate (2.45 g, 17.7 mmol) and 3-(bromomethyl)-2,4-diethylpyridine (7.1 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-{[(2,4-diethylpyridin-3-yl)methyl]sulfanyl-6-methylpyrimidin-4-ol (966 mg, 56% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 1.14-1.22 (m, 6H), 2.22 (s, 3H), 2.68 (q, J=7.5 Hz, 2H), 2.82 (q, J=7.5 Hz, 2H), 4.48 (s, 2H), 6.05 (bs, 1H), 7.08 (d, J=5.1 Hz, 1H), 8.32 (d, J=5.1 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-83157624bb514a6eb750999b979a6297
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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