Hydrochloric Acid → HCID 178436798, compound

HRID 630200Notes

Reaction equation

HRID 630200 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)=[C:7]([CH2:22][CH3:23])[CH:6]=[CH:5][N:4]=1)[CH3:2].[ClH:24].O1CCOCC1>CO>[ClH:24].[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)=[C:7]([CH2:22][CH3:23])[CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178436797HCID 178436797, compound

Product 1

HCID 178436798HCID 178436798, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(2,4-diethylpyridin-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (500 mg, 1.5 mmol) was stirred in methanol (60 mL), and a solution of 4 N HCl in dioxane (550 μL, 2.2 mmol) was added dropwise at 0° C. The mixture was stirred for 10 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-{[(2,4-diethylpyridin-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol hydrochloride (530 mg, 95% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.21-1.29 (m, 6H), 2.93 (q, J=7.5 Hz, 2H), 3.11-3.17 (m, 2H), 4.69 (s, 2H), 6.74 (s, 1H), 7.79 (d, J=6.1 Hz, 1H), 8.65 (d, J=6.1 Hz, 1H); LRMS (ES+) m/z 344 (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-7ece23608cc84e00a36736b097b00859
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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