Hydrochloric Acid → HCID 178462564, compound

HRID 630096Notes

Reaction equation

HRID 630096 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][C:5]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[N:4]1)[CH3:2].[ClH:18].O1CCOCC1>CO>[ClH:18].[CH2:1]([N:3]1[CH:7]=[CH:6][C:5]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178462563HCID 178462563, compound

Product 1

HCID 178462564HCID 178462564, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(1-ethyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (221 mg, 881 μmol) was stirred in methanol (30 mL) and a solution of 4 N HCl in dioxane (330 μL, 1.3 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 2-{[(1-ethyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol hydrochloride (243 mg, 96% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.34 (t, J=7.3 Hz, 3H), 2.25 (s, 3H), 4.08 (q, J=7.3 Hz, 2H), 4.36 (s, 2H), 6.13 (s, 1H), 6.22 (d, J=2.2 Hz, 1H), 7.66 (d, J=2.2 Hz, 1H); LRMS (ES+) m/z 251 (75%, 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-690386d91abf4f03a5db69cc3dc94dc7
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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