Triethylamine → 4-(6-Fluoro-4-pyrido[3,4-d]pyrimidinyl)-1-piperazinecarboxylic acid tert-butyl ester
Reaction equation
Cl[C:2]1[C:3]2[CH:11]=[C:10]([F:12])[N:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.FC1N=CC2N=CNC(=O)C=2C=1.C(N(CC)CC)C.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33]>[Cl-].[Na+].O.C(Cl)Cl>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:2]2[C:3]3[CH:11]=[C:10]([F:12])[N:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:33])[CH3:34]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
According to the method described in J. Med. Chem., 39:1823-1835 (1996), 4-chloro-6-fluoropyrido[3,4-d]pyrimidine was derived from 6-fluoropyrido[3,4-d]pyrimidine-4(3H)-one (1.48 g, 8.96 mmol). Triethylamine (3.75 mL, 26.9 mmol) and N-tert-butoxycarbonylpiperazine (2.00 g, 10.7 mmol) were added to a methylene chloride solution (25 mL) of this partially purified product, followed by stirring at room temperature overnight. Saturated brine was added to the reaction solution, the mixture ma was extracted with chloroform, the extract was dried over anhydrous sodium sulfate, then the solvent was evaporated and the resulting residue was purified by silica gel column chromatography to give the target compound (1.73 g, 5.20 mmol).
Workup
- extractionthe mixture ma was extracted with chloroform
- dry with materialthe extract was dried over anhydrous sodium sulfate
- customthe solvent was evaporated
- customthe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-20b312d8131947d6969eb9e882d426ee
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06423716B1
Reaction notes
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