Water → ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)amino]-5-pyrimidinecarboxylate

HRID 7419

Reaction equation

HRID 7419 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1.O>C(O)(C)C>[N:13]1([C:4]2[N:3]=[C:2]([NH:34][CH2:33][C:32]3[CH:35]=[CH:36][C:29]([F:28])=[CH:30][CH:31]=3)[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 673264-FluorobenzylamineHCID 21990788ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate

Product 1

HCID 21990825ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)amino]-5-pyrimidinecarboxylateYield 81.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (607 mg, 2.0 mmol) in isopropanol (5 mL) were added sodium carbonate (424 mg, 4 mmol) and 4-fluorobenzylamine (313 mg, 4 mmol) and the mixture was heated under reflux for 18 h. The reaction mixture was allowed to cool to room temperature and water was added. The precipitated crystals were collected by filtration, washed several times with cold water and cold ether and dried to give the title compound (637 mg, 81%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 h
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed several times with cold water and cold ether
  5. customdried

Sources & evidence

ORD record
ord-a61417b4a55b431fb3b5c4a7891ca0c1
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

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