Water → HCID 57962335, compound

HRID 541914Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][S:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]=[CH:11][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[N:36]=[C:35](Cl)[C:34]([Cl:38])=[CH:33][N:32]=1.O>CN(C)C=O>[Cl:30][C:31]1[N:36]=[C:35]([NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[CH2:5][S:6][C:7]2[CH:8]=[C:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:17])[CH3:18])[CH:10]=[CH:11][CH:12]=2)[C:34]([Cl:38])=[CH:33][N:32]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of tert-butyl {3-[(3-aminobenzyl)thio]phenyl}carbamate (0.55 g, 1.7 mmol) in N,N-dimethylformamide (5.0 mL) was treated with potassium carbonate (0.30 g, 2.2 mmol) and stirred at 25° C. for 5 min. The reaction mixture was treated with 2,4,5-trichloropyrimidine (0.25 mL, 2.2 mmol) and stirred at 25° C. for 16 h. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated and washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give a crude gum. This material was purified by flash column chromatography to give the desired product (0.67 g, 84%) as a solid. LCMS for C22H22Cl2N4O2SNa (M+Na)+: m/z=499.0, 501.0.

Workup

stirringstirred at 25° C. for 16 h
extractionextracted with ethyl acetate (100 mL)
customThe organic layer was separated
washwashed with brine (25 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated
customto give a crude gum
customThis material was purified by flash column chromatography

Sources & evidence

ORD record: ord-db805e0d5a9c4fd193f734a5c23fdd6a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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