Hydrochloric Acid → HCID 178429505, compound

HRID 577134Notes

Reaction equation

HRID 577134 reaction equation
[CH:1]1([N:7]2[C:11]([CH2:12][S:13][C:14]3[N:19]=[C:18]([OH:20])[CH:17]=[C:16]([CH3:21])[N:15]=3)=[CH:10][N:9]=[CH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:22].O1CCOCC1>CO>[ClH:22].[CH:1]1([N:7]2[C:11]([CH2:12][S:13][C:14]3[N:19]=[C:18]([OH:20])[CH:17]=[C:16]([CH3:21])[N:15]=3)=[CH:10][N:9]=[CH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429504HCID 178429504, compound

Product 1

HCID 178429505HCID 178429505, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(1-cyclohexyl-1H-imidazol-5-yl)methyl]sulfanyl)-6-methylpyrimidin-4-ol (300 mg, 986 μmol) was stirred in methanol (30 mL), and a solution of 4 N HCl in dioxane (370 μL, 1.5 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-{[(1-cyclohexyl-1H-imidazol-5-yl)methyl]sulfanyl)-6-methylpyrimidin-4-ol hydrochloride (330 mg, 98% yield); 1H NMR (500 MHz, DMSO-d6): δ 1.15-2.05 (m, 10H), 2.22 (s, 3H). 4.28-4.36 (m, 1H), 4.58 (s, 2H), 6.14 (s, 1H), 7.64 (s, 1H), 9.32 (s, 1H); LRMS (ES+) m/z 305 (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-25268f68a01d4d2c8b853192a5a150ba
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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