Benzylamine → 7-Amino-5-(3,4-dichloro-phenyl)-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid benzylamide
Reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:28][C:29]1[N:34]2[N:35]=[C:36]([C:38]([OH:40])=O)[CH:37]=[C:33]2[N:32]=[C:31]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[C:43]([Cl:48])[CH:42]=2)[CH:30]=1.[CH2:49]([NH2:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C(N(CC)CC)C>O1CCCC1.C(OCC)C>[CH2:49]([NH:56][C:38]([C:36]1[CH:37]=[C:33]2[N:32]=[C:31]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[C:43]([Cl:48])[CH:42]=3)[CH:30]=[C:29]([NH2:28])[N:34]2[N:35]=1)=[O:40])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.081 g, 0.184 mmol) was added to a suspension of 7-amino-5-(3,4-dichloro-phenyl)-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.050 g, 0.154 mmol) and benzylamine (0.034 mL, 0.308 mmol) in tetrahydrofuran (5 ml) containing triethylamine (0.064 mL, 0.462 mmol). The reaction mixture was stirred overnight at room temperature, diluted with ethyl ether (5 mL) and washed with a saturated aqueous solution of sodium bicarbonate (10 mL). The organic layer was collected, concentrated under reduced pressure and the crude product was purified by column chromatography to give 7-amino-5-(3,4-dichloro-phenyl)-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid benzylamide (0.026 g, 55%).
Workup
- washwashed with a saturated aqueous solution of sodium bicarbonate (10 mL)
- customThe organic layer was collected
- concentrationconcentrated under reduced pressure
- customthe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-17041d8ae17947f9bebc784f4a5d0031
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06833371B2
Reaction notes
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