2-Chloro-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine → 2-(4-Methoxyphenyl)-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine

HRID 1850485Notes

Reaction equation

HRID 1850485 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[C:15]([CH3:27])=[C:16]([CH3:26])[C:17]4[O:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]=4[C:24]=3[CH3:25])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](OB([O-])[O-])=[CH:32][CH:31]=1>>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([C:14]4[C:15]([CH3:27])=[C:16]([CH3:26])[C:17]5[O:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]=5[C:24]=4[CH3:25])[CH2:10][CH2:9]3)[CH:5]=[CH:4][N:3]=2)=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 594850032-Chloro-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidineHCID 86645335(4-Methoxyphenyl)borate

Product 1

HCID 594850262-(4-Methoxyphenyl)-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidineYield 23.2%

Procedure

By using 2-chloro-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine (200 mg, 0.517 mmol) synthesized in Example 82 and (4-methoxyphenyl)borate (157 mg, 1.03 mmol), the reaction was carried out in the same manner as Reference example 22 to synthesis the title compound 54.9 mg (yield 12%). Melting point was 240 to 242° C. (ethyl acetate-hexane).

Sources & evidence

ORD record
ord-0affcb00b8a24b6d801ca806d3e99ed2
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

Loading…