Hydrochloric Acid → HCID 178437157, compound

HRID 630204Notes

Reaction equation

HRID 630204 reaction equation
[CH2:1]([C:3]1[C:4]([CH2:9][S:10][C:11]2[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)=[N:5][N:6]([CH3:8])[CH:7]=1)[CH3:2].[ClH:19].O1CCOCC1>CO>[ClH:19].[CH2:1]([C:3]1[C:4]([CH2:9][S:10][C:11]2[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)=[N:5][N:6]([CH3:8])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178437156HCID 178437156, compound

Product 1

HCID 178437157HCID 178437157, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(4-ethyl-1-methyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (129 mg, 488 μmol) was stirred in methanol (20 mL), and a solution of 4 N HCl in dioxane (190 μL, 732 μmol) was added dropwise at 0° C. The mixture was stirred for 15 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-ethyl-1-methyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol hydrochloride (113 mg, 77% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.10 (t, J=7.6 Hz, 3H), 2.24 (s, 3H), 2.41 (q, J=7.0 Hz, J=0.4 Hz, 2H), 3.75 (s, 3H), 4.35 (s, 2H), 6.12 (s, 1H), 7.48 (s, 1H); LRMS (ES+) m/z 265 (40%, 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-297586f2a3794f369fb4c78fc64fd4bd
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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