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

HRID 1161665Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]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[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]=[C:4]([N:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]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-(4-chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol (3.97 g, 13.7 mmol), 3-chloro-4-methoxyaniline (2.13 g, 13.7 mmol) in 1-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.

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-ddef83b7dc6347d886462a880d3cc272
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820654B2

Reaction notes

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