3-Chloro-4-methoxyaniline → 1-[2-(3-Chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol

HRID 1161666Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[NH2:25]>C(O)CCC>[Cl:21][C:22]1[CH:23]=[C:24]([NH:25][C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]3)[CH:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=2)[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of compound 1-(2-chloro-6-phenyl-pyrimidin-4-yl)-piperidin-4-ol (3.97 g, 13.7 mmol), 3-chloro-4-methoxyaniline (2.13 g, 13.7 mmol) in butanol (30 mL) was stirred at 120° C. for 12 hours. The mixture was then cooled to temperature in the range of 20-40° C. The solid precipitated was filtered, collected, stirred in isopropanol (10 mL), filtered, and dried to give the desired compound as a white solid. Yield: 48%.

Workup

temperatureThe mixture was then cooled to temperature in the range of 20-40° C
customThe solid precipitated
filtrationwas filtered
customcollected
stirringstirred in isopropanol (10 mL)
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-353004c96050470eba23e8e4b992e39d
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820654B2

Reaction notes

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