Hydrochloric Acid → HCID 178429461, compound

HRID 630008Notes

Reaction equation

HRID 630008 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:18])[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:18][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[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 178429460HCID 178429460, compound

Product 1

HCID 178429461HCID 178429461, compoundYield 146.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(3,5-dichloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (200 mg, 662 μmol) was stirred in methanol (20 mL) and a solution of 4 N HCl in dioxane (250 μL, 993 mmol) was added dropwise at 0° C. The mixture was stirred for 30 minutes at room temperature (clear solution). The solvent was removed, and the residue was washed 3 times with diethyl ether and dried in vacuo to afford 2-{[(3,5-dichloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol hydrochloride (164 mg, 73% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.24 (s, 3H), 4.69 (s, 2H), 6.13 (s, 1H), 8.67 (s, 2H); LRMS (ES+) m/z 302 (100%, M+1), 304 (70%, 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-1553340a7be647cc8d40c2530e9fe907
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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