Hydrochloric Acid → HCID 178503525, compound

HRID 60190Notes

Reaction equation

HRID 60190 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[CH2:4][C:5]1[S:6][C:7]2[N:8]=[C:9]([S:17][CH3:18])[N:10]=[C:11]([O:14]CC)[C:12]=2[N:13]=1.O1CCOCC1.Cl>O>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[CH2:4][C:5]1[S:6][C:7]2[N:8]=[C:9]([S:17][CH3:18])[N:10]=[C:11]([OH:14])[C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 685191702-(2,6-Dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine

Product 1

HCID 178503525HCID 178503525, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 2-(2,6-dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine (1.7 g, 4.4 mmol), 1,4-dioxane (20 mL), and H2O (4 mL) was added 4 N HCl in dioxane (13 mmol, 3.3 mL) and the resulting solution was heated to 90° C. After 12 h, the solution was cooled and concentrated. The resulting residue was purified by FCC to afford the title compound (980 mg, 62%).

Workup

  1. temperaturethe solution was cooled
  2. concentrationconcentrated
  3. customThe resulting residue was purified by FCC

Sources & evidence

ORD record
ord-529ad7361ff0434ba79e441b98aa7057
Source dataset
uspto-grants-2016_09
Patent number
US09440978B2

Reaction notes

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