Hydrochloric Acid → HCID 178429468, compound

HRID 629992Notes

Reaction equation

HRID 629992 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=1.Cl.O1CCOCC1>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429467HCID 178429467, compound

Product 1

HCID 178429468HCID 178429468, compoundYield 181.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(3-chloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (100 mg, 373 μmol) was stirred in methanol (10 mL) and a solution of 4 N HCl in dioxane (140 μL, 560 mmol) was added dropwise at 0° C. The mixture was stirred for 1.5 hours at room temperature. The solvent was removed, and the residue was washed 3 times with diethyl ether and dried in vacuo to afford to 2-{[(3-chloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol hydrochloride (103 mg, 91% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.19 (s, 3H), 4.48 (s, 2H), 6.07 (bs, 1H), 7.76 (d, J=5.1 Hz, 1H), 8.53 (d, J=5.1 Hz, 1H), 8.74 (s, 1H); LRMS (ES+) m/z 268 (100%, M+1), 270 (65%, M+3).

Workup

  1. customThe solvent was removed
  2. washthe residue was washed 3 times with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e3939829320846a1a0ac265f5f197fa2
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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