2-Methoxypyrimidine-5-boronic acid → 2-(4-fluorophenyl)-N-[3-(2-methoxypyrimidin-5-yl)pyrazolo[1,5-a]pyrimidin-2-yl]acetamide

HRID 1912977Notes

Reaction equation

HRID 1912977 reaction equation
Br[C:2]1[C:3]([NH:11][C:12](=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[N:7][C:6]=12.[CH3:22][O:23][C:24]1[N:29]=[CH:28][C:27](B(O)O)=[CH:26][N:25]=1>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:12]([NH:11][C:3]2[C:2]([C:27]3[CH:26]=[N:25][C:24]([O:23][CH3:22])=[N:29][CH:28]=3)=[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][N:5]3[N:4]=2)=[O:21])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 68749921N-(3-bromopyrazolo[1,5-a]pyrimidin-2-yl)-2-(4-fluorophenyl)acetamide

Product 1

HCID 687528552-(4-fluorophenyl)-N-[3-(2-methoxypyrimidin-5-yl)pyrazolo[1,5-a]pyrimidin-2-yl]acetamide

Procedure

The product from Example 140A and 2-methoxypyrimidine-5-boronic acid were processed using the method analogous to that described in Example 110C to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.69-10.71 (m, 1H), 9.12 (dd, J=6.9, 1.7 Hz, 1H), 8.74 (s, 2H), 8.62 (dd, J=4.1, 1.7 Hz, 1H), 7.30-7.35 (m, 2H), 7.12-7.17 (m, 3H), 3.94 (s, 3H), 3.69 (s, 2H); MS (ESI) m/z 379 (M+H)+.

Sources & evidence

ORD record
ord-de409fe8dc0c4eb296b74771279969dd
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

Loading…