Diisopropylethylamine → 3-((2-chloro-5-fluoropyrimidin-4-yl)amino)-N-methylbenzamide

HRID 522933Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[NH2:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([NH:25][CH3:26])=[O:24]>C(O)(C)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:19][C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([NH:25][CH3:26])=[O:24])[C:5]([F:9])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2,4-dichloro-5-fluoropyrimidine (1 g, 5.98 mmol) in isopropanol (18 mL, 3 mL/mmol) was added DIPEA (1.6 mL, 8.9 mmol) and 3-amino-N-methylbenzamide (900 mg, 5.98 mmol) and the mixture was heated at 80° C. for 7 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 mL) and water (2×40 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography provided 3-((2-chloro-5-fluoropyrimidin-4-yl)amino)-N-methylbenzamide (800 mg, 50%) as a solid. Observed mass (M+1): 281.1

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with EtOAc (2×40 mL) and water (2×40 mL)
washThe organic extracts were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by column chromatography

Sources & evidence

ORD record: ord-98424cb1b4db4378b27470127b8ac69c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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