1,4-Dioxane hydrochloride → HCID 178462653, compound

HRID 630032Notes

Reaction equation

HRID 630032 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[CH2:10][CH2:9]2)[C:3]=1[CH2:16][S:17][C:18]1[N:23]=[C:22]([OH:24])[CH:21]=[C:20]([CH3:25])[N:19]=1.[ClH:26].O1CCOCC1>CO>[ClH:1].[ClH:26].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH2:13]2)[C:3]=1[CH2:16][S:17][C:18]1[N:23]=[C:22]([OH:24])[CH:21]=[C:20]([CH3:25])[N:19]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178462652HCID 178462652, compound

Product 1

HCID 178462653HCID 178462653, compoundYield 195.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-({[2-chloro-6-(4-ethylpiperazin-1-yl)phenyl]methyl}sulfanyl)-6-methylpyrimidin-4-ol (500 mg, 1.3 mmol) in MeOH (10 mL) was added 4 M HCl/dioxane (2 mL, 8 mmol). The mixture was stirred for 15 minutes, evaporated, and dried in vacuo, affording the title compound (575 mg, 98% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.26 (t, 3H, J=7.2 Hz), 2.24 (s, 3H), 3.15 (m, 6H), 3.22 (d, 2H, J=11.3 Hz), 3.49 (d, 2H, J=11.7 Hz), 4.67 (s, 2H), 6.11 (s, 1H), 7.19 (dd, 1H, J=1.2 Hz, 7.8 Hz), 7.29 (dd, 1H, J=1.2 Hz, 7.8 Hz), 7.34 (t, 1H, J=8.0 Hz); M+379.

Workup

  1. customevaporated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-40167f57ea344854ac12b29392549ccf
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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