Water → HCID 18381662, compound

HRID 2297446Notes

Reaction equation

HRID 2297446 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][CH2:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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][CH2:27][CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=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 18381670HCID 18381670, compound

Product 1

HCID 18381662HCID 18381662, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution under N2 of 3,5-dichloro-4-methyl-pyridine (1.28 g, 7.9 mmoles) in dry DMF (15 ml) was added under stirring at room temperature with 60% NaH (316 mg, 7.9 mmoles). The mixture was stirred for 1 hour, then dropwise added with 1-chloro-6-methoxy-5-(5phenyl-pent-1-ynyl)-phthalazine (1.33 g, 3.95 mmoles), prepared as described in example 65, 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 1:1). The separated product was taken up in ethanol (10 ml) and crystallised. The resultant product was filtered and dried under vacuum at 40° C. to give 940 mg of the title compound (yield: 51%). m.p.: 130-132° C.

Workup

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customchromatographed (eluent: petrolatum/ethyl acetate 1:1)
  5. customcrystallised
  6. filtrationThe resultant product was filtered
  7. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-e167119b48bc4ef9a41d325d18146850
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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