Hydrochloric Acid → HCID 178429479, compound

HRID 577052Notes

Reaction equation

HRID 577052 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 mmol) 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-6746bb63503847e384581fbcaea4509a
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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