HCID 66815339, compound → HCID 178429538, compound

HRID 576980Notes

Reaction equation

HRID 576980 reaction equation
Cl.[Cl:2][C:3]1[N:4]([CH2:12]Cl)[N:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2.[CH3:14][C:15]1[N:20]=[C:19]([SH:21])[N:18]=[C:17]([OH:22])[CH:16]=1>CC(C)=O.C(=O)([O-])[O-].[Ag+2]>[Cl:2][C:3]1[N:4]([CH2:12][S:21][C:19]2[N:18]=[C:17]([OH:22])[CH:16]=[C:15]([CH3:14])[N:20]=2)[N:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 66815339HCID 66815339, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429538HCID 178429538, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 180AcetoneSolvent

Procedure

3-chloro-2-(chloromethyl)-2H-indazole hydrochloride (285 mg, 1.0 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (142 mg, 1.0 mmol), and silver carbonate (550 mg, 2.0 mmol) were mixed in acetone (20 mL). The mixture was stirred at room temperature overnight. The solid was filtered. The solution was evaporated, and the crude product was purified by column chromatography to provide the titled final product (15 mg, 5% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.34 (s, 3H), 6.05 (s, 1H), 6.22 (s, 2H), 7.25 (t, 1H), 7.48 (t, 1H), 7.67 (d, 1H), 7.74 (s, 1H); M+ 307.

Workup

  1. filtrationThe solid was filtered
  2. customThe solution was evaporated
  3. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b474e2835bf547f9874a888e40295d9c
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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