N-(2-aminoethyl)acetamide → N-(6-{[2-(acetylamino)ethyl]amino)-2-phenylpyrimidin-4-yl)-2-piperidin-1-ylacetamide

HRID 895479Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][C:15](=[O:23])[CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:3]=1.[C:24]([NH:27][CH2:28][CH2:29][NH2:30])(=[O:26])[CH3:25]>CS(C)=O>[C:24]([NH:27][CH2:28][CH2:29][NH:30][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][C:15](=[O:23])[CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:3]=1)(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 130 °C

Procedure

N-(6-Chloro-2-phenylpyrimidin-4-yl)-2-piperidin-1-ylacetamide (25 mg) was dissolved in DMSO (1 ml) and N-acetylethylenediamine (78 mg) added. A reflux condenser was fitted and the mixture heated to 130° C. with stirring for 16 hrs. The reaction was cooled to room temperature and the solvent removed in vacuo. Purification via flash chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (95:5, then 93:7 v/v) yielded the title compound (18 mg).

Workup

customA reflux condenser was fitted
temperatureThe reaction was cooled to room temperature
customthe solvent removed in vacuo
customPurification via flash chromatography on silica gel
washeluting with a mixture of dichloromethane and methanol (95:5

Sources & evidence

ORD record: ord-d3827df11eb24749926ae2b3eacd5208
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916804B2

Reaction notes

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