Tetrahydrofuran → 4-(2,3-Dichlorobenzyl)-2-(methylsulfonyl)thiazolo[4,5-d]pyrimidin-7(4H)-one

HRID 1958022Notes

Reaction equation

HRID 1958022 reaction equation
[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:10]2[N:11]=[C:12](SC)[S:13][C:9]=2[C:8](=[O:16])[N:7]=[CH:6]1.O[O:23][S:24]([O-:26])=O.[K+].[CH2:28]1COCC1>O>[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:10]2[N:11]=[C:12]([S:24]([CH3:28])(=[O:26])=[O:23])[S:13][C:9]=2[C:8](=[O:16])[N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 667803804-(2,3-Dichlorobenzyl)-2-(methylthio)thiazolo[4,5-d]pyrimidin-7(4H)-one

Product 1

HCID 667800974-(2,3-Dichlorobenzyl)-2-(methylsulfonyl)thiazolo[4,5-d]pyrimidin-7(4H)-oneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-(2,3-dichlorobenzyl)-2-(methylthio)thiazolo[4,5-d]pyrimidin-7(4H)-one (660 mg, 1.842 mmol) in THF (150 mL) and water (60 mL) at 0-5° C. was added Oxone (6.8 g, 11.05 mmol). The resulting mixture was stirred at ambient temperature for 60 hours. After removing THF under reduced pressure, the precipitate formed was collected by filtration and the precipitate was further washed with water, ether and dried in vacuo to give the desired product as a white solid (574 mg, 80%). The compound was directly used in next step without further purification. 1H NMR (300 MHz, CDCl3) δ 8.53 (br, 1H), 7.54 (dd, J=7.8, 1.5 Hz, 1H), 7.35˜7.24 (m, 2H), 5.61 (s, 2H), 3.33 (s, 3H); LC-MS: 390 (MH+); IR (thin film): 3027, 3008, 2925, 1649, 1602, 1488, 1461, 1424, 1405, 1335 cm−1.

Workup

  1. customAfter removing THF under reduced pressure
  2. customthe precipitate formed
  3. filtrationwas collected by filtration
  4. washthe precipitate was further washed with water, ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8f1dab243ae7428a9276dec7839e8102
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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