2-Chloropyrimidine → HCID 90418193, compound

HRID 588277Notes

Reaction equation

HRID 588277 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10]3)[CH2:3][CH2:2]1.Cl[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1.CCN(C(C)C)C(C)C>CCO>[N:19]1[CH:20]=[CH:21][CH:22]=[N:23][C:18]=1[N:1]1[CH2:2][CH2:3][CH:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10]3)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 68798350HCID 68798350, compound

Product 1

HCID 90418193HCID 90418193, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(piperidin-4-yl)indolin-2-one (39.8 mg, 0.184 mmol) in EtOH 3 ml) were added 2-chloropyrimidine (33.7 mg, 0.294 mmol) and iPr2NEt (0.095 ml, 0.551 mmol). After stirring at 80° C. for 6 h, the reaction mixture was concentrated. The residue was purified by column chromatography (CHCl3/MeOH) to give 5-(1-(pyrimidin-2-yl)piperidin-4-yl)indolin-2-one (47.9 mg, 88%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-0292be11a0da4e44ae5266e383848592
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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