Potassium Carbonate → HCID 178429540, compound

HRID 577055Notes

Reaction equation

HRID 577055 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][N:18]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[N:19]1>CN(C=O)C>[CH3:24][C:20]1[CH:21]=[C:22]([CH3:23])[N: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]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59589438HCID 59589438, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429540HCID 178429540, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (1.2 g, 8.8 mmol) was dissolved in anhydrous DMF (50 mL), then potassium carbonate (3.6 g, 26.3 mmol) and 1-(bromomethyl)-3,5-dimethyl-1H-pyrazole (3.0 g, 15.8 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 10% DCM in MeOH to afford 2-{[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]sulfanyl)-6-methylpyrimidin-4-ol (218 mg, 10% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6) δ 2.12 (s, 3H), 2.22 (s, 3H), 2.30 (s, 3H), 5.81 (s, 2H), 5.83 (s, 6.07 (bs, 1H); LRMS (ES+) m/z 251 (50%, 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 10% DCM in MeOH

Sources & evidence

ORD record
ord-cd6b389fabdc41f69d75fdb8f08a042b
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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