Hydrochloric Acid → HCID 178463039, compound

HRID 577132Notes

Reaction equation

HRID 577132 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[CH:6][CH:5]=[N:4]1)[CH3:2].[ClH:18].O1CCOCC1>CO>[ClH:18].[CH2:1]([N:3]1[C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[CH:6][CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178463038HCID 178463038, compound

Product 1

HCID 178463039HCID 178463039, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(1-ethyl-1H-pyrazol-5-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (150 mg, 600 μmol) was stirred in methanol (20 mL) and a solution of 4 N HCl in dioxane (225 μL, 900 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-{[(1-ethyl-1H-pyrazol-5-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol hydrochloride (170 mg, 100% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.30 (t, J=7.0 Hz, 3H), 2.21 (s, 3H), 4.15 (q, J=7.0 Hz, 2H), 4.50 (s, 2H), 6.11 (s, 1H), 6.25 (d, J=1.7 Hz, 1H), 7.37 (d, J=1.7 Hz, 1H); LRMS (ES+) m/z 251 (50%, 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-5ce0a1ba9b244e6a912216529fb555ec
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…