Diisopropylethylamine → N-[1-(6-aminopyrimidin-4-yl)piperidin-3-yl]-2,2,2-trifluoroacetamide

HRID 1241372Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C(N(C(C)C)CC)(C)C.[F:18][C:19]([F:30])([F:29])[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1)=[O:21]>C(O)CCC>[NH2:8][C:4]1[N:5]=[CH:6][N:7]=[C:2]([N:25]2[CH2:26][CH2:27][CH2:28][CH:23]([NH:22][C:20](=[O:21])[C:19]([F:18])([F:29])[F:30])[CH2:24]2)[CH:3]=1

Participants

Conditions

Temperature: 170 °C

Procedure

6-Chloropyrimidin-4-amine 7-2 (0.149 g, 1.15 mmol) and diisopropylethylamine (0.446 g, 3.45 mmol) were suspended in n-butanol. 2,2,2-Trifluoro-N-piperidin-3-ylacetamide 9-3 (0.226 g, 1.15 mmol) was then added. The reaction was stirred at 170° C. for 24 hours. The butanol was then removed under reduced pressure and the product was purified on a silica column eluted with DCM:MeOH:NH4OH (95:5:0.5). 1H-NMR (CD3OD): 8.06 ppm (s, 1H); 5.82 ppm (s, 1H); 4.27 ppm (d, 1H); 4.15 ppm (d, 1H); 3.85 ppm (m, 1H); 3.73 ppm (p, 3H); 3.23 ppm (q, 3H); 3.08 ppm (dd, 2H); 2.13 ppm (m, 1H); 1.85 ppm (m, 1H); 1.71 ppm (m, 1H); 1.62 ppm (m, 1H).

Workup

customThe butanol was then removed under reduced pressure
customthe product was purified on a silica column
washeluted with DCM:MeOH:NH4OH (95:5:0.5)

Sources & evidence

ORD record: ord-ce0119a0ffc0439fafe648baeaa002f0
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115597B2

Reaction notes

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