Hydrochloric Acid → HCID 178478917, compound

HRID 577144Notes

Reaction equation

HRID 577144 reaction equation
[Cl:1][C:2]1[C:3]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([F:20])([F:19])[F:18])[N:11]=2)=[N:4][N:5]([CH3:7])[CH:6]=1.Cl.O1CCOCC1>CO>[ClH:1].[Cl:1][C:2]1[C:3]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([F:20])([F:18])[F:19])[N:11]=2)=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178480367HCID 178480367, compound

Product 1

HCID 178478917HCID 178478917, compoundYield 127.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(4-chloro-1-methyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (120 mg, 370 μmol) was stirred in methanol (15 mL) and a solution of 4 N HCl in dioxane (140 μL, 554 μmol) 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-{[(4-chloro-1-methyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol hydrochloride (85 mg, 63% yield); 1H NMR (400 MHz, DMSO-d6): δ 3.78 (s, 3H), 4.39 (s, 2H), 6.66 (s, 1H), 7.94 (s, 1H); LRMS (ES+) m/z 325 (10%, 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-03439e42ea9048178c547bb53c3f5a83
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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