Hydrochloric Acid → HCID 178429501, compound

HRID 630100Notes

Reaction equation

HRID 630100 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][S:8][C:9]2[N:14]=[C:13]([OH:15])[CH:12]=[C:11]([CH3:16])[N:10]=2)=[CH:5][N:4]=[C:3]1[CH3:17].[ClH:18].O1CCOCC1>CO>[ClH:18].[CH3:1][N:2]1[C:6]([CH2:7][S:8][C:9]2[N:14]=[C:13]([OH:15])[CH:12]=[C:11]([CH3:16])[N:10]=2)=[CH:5][N:4]=[C:3]1[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429500HCID 178429500, compound

Product 1

HCID 178429501HCID 178429501, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(1,2-dimethyl-1H-imidazol-5-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (390 mg, 1.6 mmol) was stirred in methanol (50 mL), and a solution of 4 N HCl in dioxane (580 μL, 2.3 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-{[(1,2-dimethyl-1H-imidazol-5-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol hydrochloride (412 mg, 92% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.23 (s, 314), 2.55 (s, 3H), 3.68 (s, 3H), 4.48 (s, 2H), 6.12 (s, 1H), 7.51 (s, 1H); LRMS (ES+) m/z 251 (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-3e184efce54b4f0cbbcea763b951c93d
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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