Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 3,5-Dichloro-4-methylpyridine | HCID 10953827 | — |
| Reactant | HCID 54335011 | HCID 54335011 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 54153966 | HCID 54153966 | 60.2% |
Reaction Steps
A solution under N2 of 3,5-dichloro-4-methyl-pyridine (0.768 g, 4.74 mmoles) in dry DMF (10 ml) was added under stirring at room temperature with 60% NaH (189.6 mg, 4.74 mmoles) and the mixture was stirred for 1 hour, then dropwise added with 1-chloro-6-methoxy-5-phenylethynyl-phthalazine (700 mg, 2.37 mmoles), prepared as described in example 61, in dry DMF (20 ml). After 3 hours the mixture was poured into water, extracted with ethyl acetate, washed with water, anhydrified over Na2SO4 and brought to dryness. The residue was flash chromatographed (eluent: petrolatum/ethyl acetate 3:7). The separated product was taken up in ethyl ether and crystallised from 30 ml of ethyl acetate/CH2Cl2 to give 600 mg of the title compound (yield: 60%). m.p.: 217-219° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06329370B1 |
|---|
| Source dataset | uspto-grants-2001_12 |
|---|
| ORD ID | ord-4ecb5e89056d46169547185ed2835637 |
|---|
| Source note | uspto-grants-2001_12 |
|---|