Hydrochloric Acid → HCID 178436796, compound

HRID 630195Notes

Reaction equation

HRID 630195 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]([CH3:18])[N:12]=2)=[C:7]([CH2:19][CH3:20])[CH:6]=[CH:5][N:4]=1)[CH3:2].[ClH:21].O1CCOCC1>CO>[ClH:21].[CH2:1]([C:3]1[C:8]([CH2:9][S:10][C:11]2[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)=[C:7]([CH2:19][CH3:20])[CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178436795HCID 178436795, compound

Product 1

HCID 178436796HCID 178436796, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(2,4-diethylpyridin-3-yl)methyl]sulfanyl-6-methylpyrimidin-4-ol (430 mg, 1.5 mmol) was stirred in methanol (65 mL) and a solution of 4 N HCl in dioxane (560 μL, 2.22 mmol) 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-{[(2,4-diethylpyridin-3-yl)methyl]sulfanyl-6-methylpyrimidin-4-ol hydrochloride (466 mg, 96% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.25-1.35 (m, 6H), 2.24 (s, 3H), 2.97 (q, J=7.6 Hz, 2H), 3.18 (q, J=7.6 Hz, 2H), 4.67 (s, 2H), 6.14 (s, 1H), 7.82 (d, J=6.1 Hz, 1H), 8.67 (d, J=6.1 Hz, 1H); LRMS (ES+) m/z 290 (35%, 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-fece11564b6f46dfa332d850d5becb80
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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