Hydrochloric Acid → HCID 178429458, compound

HRID 630183Notes

Reaction equation

HRID 630183 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[C:3]=1[CH2:11][S:12][C:13]1[N:18]=[C:17]([OH:19])[CH:16]=[C:15]([CH3:20])[N:14]=1.Cl.O1CCOCC1>CO>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH3:9])[CH3:10])[C:3]=1[CH2:11][S:12][C:13]1[N:18]=[C:17]([OH:19])[CH:16]=[C:15]([CH3:20])[N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429457HCID 178429457, compound

Product 1

HCID 178429458HCID 178429458, compoundYield 202.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-({[4-chloro-2-(propan-2-yl)pyridin-3-yl]methyl}sulfanyl)-6-methylpyrimidin-4-ol (176 mg, 570 μmol) was stirred in methanol (20 mL), and a solution of 4 N HCl in dioxane (215 μL, 855 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-({[4-chloro-2-(propan-2-yl)pyridin-3-yl]methyl}sulfanyl)-6-methylpyrimidin-4-ol hydrochloride (200 mg, 100% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.28 (d, J=6.7 Hz, 6H), 2.26 (s, 3H), 3.56-3.68 (m, 1H), 4.70 (s, 2H), 6.14 (s, 1H), 7.69 (d, J=5.5 Hz, 1H), 8.55 (d, J=5.5 Hz, 1H); LRMS (ES+) m/z 310 (15%, 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-93b12d2b2191436ea2e92cd78e038f13
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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