1,4-Dioxane hydrochloride → 6-methyl-2-[(5-methyl-3-propan-2-ylimidazol-4-yl)methylsulfanyl]-1H-pyrimidin-4-one;hydrochloride

HRID 630129Notes

Reaction equation

HRID 630129 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[CH:13]=[N:12][C:11]=2[CH3:18])[N:5]=[C:4]([OH:19])[CH:3]=1.[ClH:20].O1CCOCC1>CO>[ClH:20].[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:14]([CH:15]([CH3:16])[CH3:17])[CH:13]=[N:12][C:11]=2[CH3:18])[N:5]=[C:4]([OH:19])[CH:3]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178429475HCID 178429475, compound

Product 1

HCID 1784294766-methyl-2-[(5-methyl-3-propan-2-ylimidazol-4-yl)methylsulfanyl]-1H-pyrimidin-4-one;hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 6-methyl-2-({[4-methyl-1-(propan-2-yl)-1H-imidazol-5-yl]methyl}-sulfanyl)pyrimidin-4-ol (200 mg, 0.72 mmol) in MeOH (3 mL) was added 4 M HCl/dioxane (1 mL, 4.0 mmol). The mixture was filtered to remove particles in suspension. The solution was evaporated and dried in vacuo, affording the title compound (208 mg, 92% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.49 (d, 3H, J=6.7 Hz), 2.23 (s, 3H), 2.36 (s, 3H), 4.60 (s, 2H), 4.75 (m, 1H), 6.10 (s, 1H), 9.24 (s, 1H); M+279.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove particles in suspension
  3. customThe solution was evaporated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2040140647a54818b2e26909c560dfb3
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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