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

HRID 577154Notes

Reaction equation

HRID 577154 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]([C:19]([F:22])([F:21])[F:20])[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]([C:19]([F:22])([F:20])[F:21])[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178437620HCID 178437620, compound

Product 1

HCID 1784376212-[(4-chloro-2-ethyl-3-pyridinyl)methylsulfanyl]-6-(trifluoromethyl)-1H-pyrimidin-4-one;hydrochlorideYield 175.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(4-chloro-2-ethylpyridin-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (165 mg, 472 μmol) was stirred in methanol (20 mL) and a solution of 4 N HCl in dioxane (180 μL, 708 μmol) 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-(trifluoromethyl)pyrimidin-4-ol hydrochloride (160 mg, 88% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.21 (t, J=7.4 Hz, 3H), 3.05 (q, J=7.4 Hz, 2H), 4.69 (s, 2H), 6.71 (s, 1H), 7.71 (d, J=5.7 Hz, 1H), 8.53 (d, J=5.7 Hz, 1H); LRMS (ES+) m/z 350 (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-e8f891637d4d4e67a4a91b55342a45c4
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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