Water → Ethyl 6-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylate

HRID 74559Notes

Reaction equation

HRID 74559 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:20]([OH:29])[NH:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[O:29]=[C:20]1[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=3)[CH2:14][CH2:15]2)=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 22756838Ethyl 6-chloropyrimidine-4-carboxylateHCID 673376243-Piperidin-4-yl-1,2-dihydro-quinolin-2-ol

Product 1

HCID 58386736Ethyl 6-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

730 mg (3.91 mmol) ethyl 6-chloropyrimidine-4-carboxylate were placed in 10 mL DMF. 900 mg (3.94 mmol) 3-piperidin-4-yl-1,2-dihydro-quinolin-2-ol and 2.30 mL (13.4 mmol) DIPEA were added and the reaction mixture was stirred overnight at RT. The reaction mixture was mixed with 60 mL water and stirred for 30 min. The precipitated solid was suction filtered and dried.

Workup

  1. stirringstirred for 30 min
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-2af5a626b26641d5b8965c6ccdce442c
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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