Hydrochloric Acid → HCID 178437120, compound

HRID 577183Notes

Reaction equation

HRID 577183 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH3:18])[N:12]=1)[CH3:2].[ClH:19].O1CCOCC1>CO>[ClH:19].[CH2:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH3:18])[N:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178437119HCID 178437119, compound

Product 1

HCID 178437120HCID 178437120, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(3-ethylpyridin-4-yl)methyl]sulfanyl)-6-methylpyrimidin-4-ol (100 mg, 383 μmol) was stirred in methanol (20 mL) and a solution of 4 N HCl in dioxane (145 μL, 574 μmol) was added dropwise at 0° C. The mixture was stirred for 15 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-{[(3-ethylpyridin-4-yl)methyl]sulfanyl)-6-methylpyrimidin-4-ol hydrochloride (110 mg, 97% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.28 (t, J=7.5 Hz, 3H), 2.15 (s, 3H), 2.98 (q, J=7.5 Hz, 2H), 4.62 (s, 2H), 6.08 (s, 1H), 8.12 (d, J=6.0 Hz, 1H), 8.70 (d, J=6.0 Hz, 1H), 8.77 (s, 1H); LRMS (ES+) m/z 262 (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-bf9928368c1a4d9a962030bd419c4e07
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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