Potassium Carbonate → HCID 178429478, compound

HRID 577051Notes

Reaction equation

HRID 577051 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]([CH3:25])=[N:20][N:21]([CH3:24])[C:22]=1[Cl:23]>CN(C=O)C>[Cl:23][C:22]1[N:21]([CH3:24])[N:20]=[C:19]([CH3:25])[C:18]=1[CH2:17][S:8][C:6]1[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17862311HCID 17862311, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429478HCID 178429478, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (437 mg, 3.0 mmol) was dissolved in anhydrous DMF (25 mL), then potassium carbonate (1.27 g, 9.2 mmol) and crude 4-(bromomethyl)-5-chloro-1,3-dimethyl-1H-pyrazole (1.03 g, 4.6 mmol) were added. The mixture was stirred for 3 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 10% DCM/MeOH to afford 2-{[(5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (190 mg, 22% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 2.17 (s, 3H), 2.20 (s, 3H), 3.70 (s, 3H), 4.20 (s, 2H), 5.76 (bs, 1H); LRMS (ES+) m/z 285 (80%, M+1), 287 (30%, M+3).

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/MeOH

Sources & evidence

ORD record
ord-b5ba0dc3be76424cad64dddb04802fe3
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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