Diisopropylethylamine → HCID 86585955, compound

HRID 1241385Notes

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.[C@H:18]12[CH2:24][C@H:21]([NH:22][CH2:23]1)[CH2:20][N:19]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>C(O)CCC>[NH2:8][C:4]1[N:5]=[CH:6][N:7]=[C:2]([N:22]2[CH2:23][C@@H:18]3[CH2:24][C@H:21]2[CH2:20][N:19]3[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

6-Chloropyrimidin-4-amine 7-2 (0.222 g, 1.71 mmol) and diisopropylethylamine (0.222 g, 1.71 mmol) were suspended in n-butanol. tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 16-1 (0.34 g, 1.71 mmol) was then added. The reaction was stirred at 150° C. for 18 hours and then the product was purified on a silica column. 1H-NMR (DMSO): 7.91 ppm (s, 1H); 6.18 ppm (s, 2H); 5.33 ppm (s, 1H); 4.72 ppm (s, 1H); 4.41 ppm (d, 1H); 3.40 ppm (t, 1H); 3.27 ppm (m, 1H); 3.12 ppm (m, 2H); 1.86 ppm (m, 2H); 1.40 ppm (s, 4H); 1.36 ppm (s, 5H).

Workup

customthe product was purified on a silica column

Sources & evidence

ORD record: ord-9eed996c9e964ecba3ec1ed41953d3f7
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115597B2

Reaction notes

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