Potassium Carbonate → HCID 178462563, compound

HRID 630095Notes

Reaction equation

HRID 630095 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:22]=[CH:21][N:20]([CH2:23][CH3:24])[N:19]=1>CN(C=O)C>[CH2:23]([N:20]1[CH:21]=[CH:22][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]1)[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59589448HCID 59589448, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178462563HCID 178462563, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (341 mg, 2.4 mmol) was dissolved in anhydrous DMF (20 mL), then potassium carbonate (995 mg, 7.2 mmol) and 3-(bromomethyl)-1-ethyl-1H-pyrazole (590 mg, 3.1 mmol) were added. The mixture was stirred for 2.5 hours 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 8% DCM in MeOH to afford 2-{[(1-ethyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (235 mg, 39% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 1.34 (t, J=7.2 Hz, 3H), 2.20 (s, 3H), 4.07 (q, J=7.3 Hz, 2H), 4.32 (s, 2H), 5.99 (bs, 1H), 6.19 (d, J=2.2 Hz, 1H), 7.63 (d, J=2.2 Hz, 1H); LRMS (ES+) m/z 251 (100%, 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 8% DCM in MeOH

Sources & evidence

ORD record
ord-2d1e6778a44341b786323311f9877993
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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