Tert-butyl 2-[4-(2-aminopyrimidin-5-yl)-2-fluorophenoxy]propionate → Tert-butyl 2-[2-fluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]phenoxy]propanoate

HRID 500152Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:23]=[CH:22][C:11]([O:12][CH:13]([CH3:21])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:10]([F:24])[CH:9]=2)=[CH:4][N:3]=1.Cl[CH:26]([C:29]1([C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[N:38]=[CH:37][CH:36]=[CH:35]3)[CH2:31][CH2:30]1)[CH:27]=O>C(O)(C)C>[F:24][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[N:7][C:2]3[N:3]([C:26]([C:29]4([C:32]5[CH:33]=[C:34]6[C:39](=[CH:40][CH:41]=5)[N:38]=[CH:37][CH:36]=[CH:35]6)[CH2:31][CH2:30]4)=[CH:27][N:1]=3)[CH:4]=2)[CH:23]=[CH:22][C:11]=1[O:12][CH:13]([CH3:21])[C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl 2-[4-(2-aminopyrimidin-5-yl)-2-fluorophenoxy]propanoate (0.33 g, 1.0 mmol) and chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde (0.24 g, 1.0 mmol) in isopropanol was heated at 100° C. overnight. After cooling to RT, the mixture was purified by RP-HPLC (pH 2.0) to afford the desired product (0.22 g, 42%). LCMS: (M+H)=525.2.

Workup

temperatureAfter cooling to RT
customthe mixture was purified by RP-HPLC (pH 2.0)

Sources & evidence

ORD record: ord-63b40e46fb164095b0e597f6485391c2
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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