Potassium Carbonate → HCID 178437156, compound

HRID 577160Notes

Reaction equation

HRID 577160 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:22]([CH2:23][CH3:24])=[CH:21][N:20]([CH2:25]C)[N:19]=1>CN(C=O)C>[CH2:23]([C:22]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)=[N:19][N:20]([CH3:25])[CH:21]=1)[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59589336HCID 59589336, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178437156HCID 178437156, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (604 mg, 4.2 mmol) was dissolved in anhydrous DMF (30 mL), and then potassium carbonate (1.76 g, 12.8 mmol) and 3-(bromomethyl)-1,4-diethyl-1H-pyrazole (5.1 mmol) 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 4-12% DCM/MeOH to afford 2-{[(4-ethyl-1-methyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (454 mg, 41% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 1.07 (t, J=7.4 Hz, 3H), 2.17 (s, 3H), 2.37 (q, J=7.4 Hz, 2H), 3.70 (s, 3H), 4.29 (s, 2H), 6.00 (s, 1H), 7.41 (s, 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 4-12% DCM/MeOH

Sources & evidence

ORD record
ord-dbd684bccd494b6aa3b455eff6c4de22
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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