Hydrochloric Acid → HCID 178429488, compound

HRID 577041Notes

Reaction equation

HRID 577041 reaction equation
[N:1]1[C:2]([CH2:10][S:11][C:12]2[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH3:19])[N:13]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[ClH:20].O1CCOCC1>CO>[ClH:20].[N:1]1[C:2]([CH2:10][S:11][C:12]2[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH3:19])[N:13]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429487HCID 178429487, compound

Product 1

HCID 178429488HCID 178429488, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-({imidazo[1,2-a]pyridin-2-ylmethyl}sulfanyl)-6-methylpyrimidin-4-ol (100 mg, 367 μmol) was stirred in methanol (10 mL), and a solution of 4 N HCl in dioxane (140 μL, 551 μmol) was added dropwise at 0° C. The mixture was stirred for 1 hour at room temperature. The solvent was removed by evaporation, and the residue was triturated with diethyl ether and dried in vacuo to afford to 2-({imidazo[1,2-a]pyridin-2-ylmethyl}sulfanyl)-6-methylpyrimidin-4-ol hydrochloride (118 mg, 100% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.25 (s, 3H), 4.62 (s, 2H), 6.11 (s, 1H), 6.84 (dt, J=2.1 Hz, J=6.4 Hz, 1H), 7.88-7.94 (m, 2H), 8.30 (s, 1H), 8.88 (d, J=6.8 Hz, 1H); LRMS (ES+) m/z 273 (100%, M+1).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was triturated with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-d7592b0b387f44d6a8a51627be5a7e76
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…