Phenylacetyl chloride → 5-chloro-2-(methylsulfanyl)-N'-(phenylacetyl)pyrimidine-4-carbohydrazide

HRID 2267422Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:10]([NH:12][NH2:13])=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[C:14]1([CH2:20][C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.O>[Cl:1][C:2]1[C:3]([C:10]([NH:12][NH:13][C:21](=[O:22])[CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5-Chloro-2-(methylthio)pyrimidine-4-carbohydrazide (1.0 g, 4.6 mmol) and 2-phenylacetyl chloride (0.61 mL, 4.6 mmol) were dissolved in 20 mL pyridine. The solution was stirred at 60° C. for 3 h. Upon cooling to room temperature, the reaction mixture was diluted with excess H2O. The aqueous layer was extracted with EtOAc 3 times. The combined organic layers were washed with 2 N HCl and H2O, dried over magnesium sulfate and concentrated under vacuum. Flash chromatography was required to obtain 0.442 g (26% yield) of product as a white solid. MS (M+H)+ 337.

Workup

temperatureUpon cooling to room temperature
extractionThe aqueous layer was extracted with EtOAc 3 times
washThe combined organic layers were washed with 2 N HCl and H2O
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-730621f8196b4fac8f3cd21216bb1e8c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Reaction notes

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