Water → HCID 86686754, compound

HRID 1403120Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[NH2:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].C(N(CC)C(C)C)(C)C.O>CC(N(C)C)=O>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4,6-Dichloro-2-(methylsulfanyl)pyrimidine (50 mg) and tert-butyl (2-amino-4-methylphenyl)carbamate (57 mg) were dissolved in dimethylacetamide (250 μL), and N,N-diisopropyl ethylamine (69 μL) was added thereto, followed by stirring at 100° C. for 7 hours. After the completion of the reaction, the mixture was cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The extracts were washed with saturated brine, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane) to obtain a desired compound tert-butyl (2-{[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]amino}-4-methylphenyl)carbamate (50 mg) as a white powder.

Workup

customAfter the completion of the reaction
temperaturethe mixture was cooled to room temperature
extractionfollowed by extraction with ethyl acetate
washThe extracts were washed with saturated brine
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record: ord-dc0d485005954c8dabda5dba7dded3e7
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912180B2

Reaction notes

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