Hydrochloric Acid → 2-[(4-chloro-2-ethyl-3-pyridinyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one;hydrochloride

HRID 630191Notes

Reaction equation

HRID 630191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=1[CH2:10][S:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH3:19])[N:13]=1.Cl.O1CCOCC1>CO>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=1[CH2:10][S:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH3:19])[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178437618HCID 178437618, compound

Product 1

HCID 1784376192-[(4-chloro-2-ethyl-3-pyridinyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one;hydrochlorideYield 200%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(4-chloro-2-ethylpyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (260 mg, 879 μmol) was stirred in methanol (30 mL) and a solution of 4 N HCl in dioxane (330 μL, 1.32 mmol) was added dropwise 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-{[(4-chloro-2-ethylpyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol hydrochloride (292 mg, 100% yield); 1H NMR (400 MHz, DMSO-d6) δ 1.27 (t, J=7.4 Hz, 3H), 2.25 (s, 3H), 3.15-3.21 (m, 2H), 4.69 (s, 2H), 6.12 (s, 1H), 7.87 (d, J=5.9 Hz, 1H), 8.61 (d, J=5.9 Hz, 1H); LRMS (ES+) m/z 296 (20%, 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-6089ee90665a4ea09b1b960451a31df2
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…