Hydrochloric Acid → HCID 178429492, compound

HRID 577222Notes

Reaction equation

HRID 577222 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:19]=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:5]=[C:4]([OH:20])[CH:3]=1.[ClH:21].O1CCOCC1>CO>[ClH:21].[ClH:21].[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:19]=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:5]=[C:4]([OH:20])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429491HCID 178429491, compound

Product 1

HCID 178429492HCID 178429492, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-2-[(quinoxalin-2-ylmethyl)sulfanyl]pyrimidin-4-ol (250 mg, 879 μmol) was stirred in methanol (25 mL) and a solution of 4 N HCl in dioxane (660 μL, 2.63 mmol) was added dropwise at 0° C. The mixture was stirred for 20 minutes at room temperature. The solvent was removed by evaporation, and the residue was triturated with diethyl ether, filtered, washed with ether, and dried in vacuo to afford 6-methyl-2-[(quinoxalin-2-ylmethyl)sulfanyl]pyrimidin-4-ol dihydrochloride (289 mg, 92% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 4.74 (s, 2H), 6.10 (s, 1H), 7.82-7.89 (m, 2H), 8.03-8.11 (m, 2H), 9.12 (s, 1H); LRMS (ES+) m/z 285 (100%, M+1).

Workup

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

Sources & evidence

ORD record
ord-20da1cecdcd44c3a9e8e5c0190ea532a
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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