Hydrochloric Acid → HCID 178429479, compound

HRID 630094Notes

Reaction equation

HRID 630094 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH3:18])[N:12]=1.[ClH:19].O1CCOCC1>CO>[ClH:1].[ClH:19].[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH3:18])[N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429478HCID 178429478, compound

Product 1

HCID 178429479HCID 178429479, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol, (150 mg, 527 μmol) was stirred in methanol (30 mL) and a solution of 4 N HCl in dioxane (395 μL, 1.6 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 to 2-{[(5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol dihydrochloride (143 mg, 76% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.18 (s, 3H), 2.23 (s, 3H), 3.70 (s, 3H), 4.21 (s, 2H), 6.09 (s, 1H); LRMS (ES+) m/z 285 (40%, M+1), 287 (15%, M+3).

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-77ea1b79b15e4d3d86a1fb14f705b0d7
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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