Benzoyl bromide → HCID 18507507, compound

HRID 1356184Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4]([S:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:3]=1.[C:24](Br)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:24]([N:1]([C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4]([S:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:3]=1)[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 200 mg (0.62 mmol) 2-amino-4-furan-2-yl-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile and 8 mg (0.06 mmol) 4-dimethylaminopyridine in 2 ml pyridine was added dropwise 0.73 ml (6.18 mmol) benzoyl bromide and the reaction mixture stirred at 50° C. for 3 hours. The reaction mixture was then cooled to room temperature and partitioned between water and ethyl acetate. The combined organic phases were dried with sodium sulfate and concentrated in vacuo. Chromatography (1/2 ethyl acetate/hexane then 1/1 ethyl acetate/hexane then ethyl acetate) followed by trituration in ether afforded 100 mg (30%) N-benzoyl-N-[5-cyano-4-furan-2-yl-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidin-2-yl]-benzamide as a white crystalline solid. ES-MS m/e (%): 532 (M+H+, 68).

Workup

temperatureThe reaction mixture was then cooled to room temperature
custompartitioned between water and ethyl acetate
dry with materialThe combined organic phases were dried with sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6f4bfdde7d8c4038a638be5f6dccf09a
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

Loading…