Hydrochloric Acid → HCID 178429518, compound

HRID 577062Notes

Reaction equation

HRID 577062 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=3[N:11]=2)[N:5]=[C:4]([OH:22])[CH:3]=1.[ClH:23].O1CCOCC1>CO>[ClH:23].[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=3[N:11]=2)[N:5]=[C:4]([OH:22])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429517HCID 178429517, compound

Product 1

HCID 178429518HCID 178429518, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-2-({[1-(propane-2-yl)-1H-benzimidazol-2-yl]methyl}sulfanyl)pyrimidin-4-ol (500 mg, 1.6 mmol) was stirred in methanol (50 mL) and a solution of 4 N HCl in dioxane (600 μL, 2.4 mmol) was added dropwise at 0° C. The mixture was stirred for 1 hour at room temperature. The solvent was removed by evaporation, and the residue was triturated with diethyl ether and dried in vacuo to afford 6-methyl-2-({[1-(propane-2-yl)-1H-benzimidazol-2-yl]methyl}sulfanyl)pyrimidin-4-ol hydrochloride (560 mg, 100% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.68 (s, 3H), 1.70 (s, 3H), 2.14 (s, 3H), 5.01 (s, 2H), 5.21-5.28 (m, 1H), 6.20 (s, 1H), 7.54-7.61 (m, 2H), 7.84-7.87 (m, 1H), 8.16-8.19 (m, 1H); LRMS (ES+) m/z 315 (100%, 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-c64a0247960d46dc846fce8975ef9025
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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