Hydrochloric Acid → HCID 178437598, compound

HRID 577155Notes

Reaction equation

HRID 577155 reaction equation
[CH2:1]([C:3]1[C:8]([CH2:9][S:10][C:11]2[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([C:18]([F:21])([F:20])[F:19])[N:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].[ClH:22].O1CCOCC1>CO>[ClH:22].[CH2:1]([C:3]1[C:8]([CH2:9][S:10][C:11]2[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([C:18]([F:21])([F:20])[F:19])[N:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178437597HCID 178437597, compound

Product 1

HCID 178437598HCID 178437598, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(2-ethylpyridin-3-yl)methyl]sulfanyl)-6-(trifluoromethyl)pyrimidin-4-ol (218 mg, 694 μmol) was stirred in methanol (30 mL), and a solution of 4 N HCl in dioxane (260 μL, 1.04 mmol) was dropwise added at 0° C. The mixture was stirred for 30 minutes at room temperature. The solvent was removed by evaporation, and the residue was triturated with diethyl ether and dried in vacuo to afford 2-{[(2-ethylpyridin-3-yl)methyl]sulfanyl)-6-(trifluoromethyl)pyrimidin-4-ol hydrochloride (225 mg, 92% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.28 (t, J=7.6 Hz, 3H), 3.11-3.17 (m, 2H), 4.58 (s, 2H), 6.65 (s, 1H), 7.77 (q, J=5.9 Hz, J=1.8 Hz, 1H), 8.49 (d, J=7.8 Hz, 1H), 8.39 (d, J=5.5 Hz 1H).

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-bcd44b6f4172474884637bf4891cb53a
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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