Water → HCID 54153966, compound

HRID 2297443Notes

Reaction equation

HRID 2297443 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[C:18]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]=1.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH2:8][C:13]1[C:22]2[C:17](=[C:18]([C:25]#[C:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 109538273,5-Dichloro-4-methylpyridineHCID 54335011HCID 54335011, compound

Product 1

HCID 54153966HCID 54153966, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customchromatographed (eluent: petrolatum/ethyl acetate 3:7)
  5. customcrystallised from 30 ml of ethyl acetate/CH2Cl2

Sources & evidence

ORD record
ord-2ef2c5280b2c4f3ea201e8975354c08d
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

Loading…