Hydrochloric Acid → HCID 178437132, compound

HRID 630233Notes

Reaction equation

HRID 630233 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:9][S:10][C:11]2[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)[CH:6]=[N:7][CH:8]=1)[CH3:2].[ClH:19].O1CCOCC1.CCOCC>CO>[ClH:19].[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:9][S:10][C:11]2[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)[CH:6]=[N:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 178437131HCID 178437131, compound

Product 1

HCID 178437132HCID 178437132, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2-{[(5-ethylpyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (1.0 g, 3.82 mmol) was stirred in methanol (10 mL), and a solution of 4 N HCl in dioxane (2.86 mL, 11.47 mmol) was added dropwise at 0° C. The mixture was stirred for 5 minutes at 0° C. Anhydrous ether (25 mL) was added to precipitate the salt, which was filtered and washed with anhydrous ether to provide 2-{[(5-ethylpyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol hydrochloride as a white solid (1.08 g, 95% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.23 (t, 3H), 2.23 (s, 3H), 2.81 (q, 2H), 4.49 (s, 2H), 6.09 (bs, 1H), 8.69 (s, 1H), 8.73 (s, 1H), 8.89 (s, 1H); M+261.5.

Workup

  1. customto precipitate the salt, which
  2. filtrationwas filtered
  3. washwashed with anhydrous ether

Sources & evidence

ORD record
ord-fa30671f26614e6c9f443f451604ce8b
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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