Sodium hydride → 1-(3,5-Dichloro-pyridin-4-ylmethyl)-4-ethyl-6-methoxy-phthalazine

HRID 2297405Notes

Reaction equation

HRID 2297405 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](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[C:16]([CH2:25][CH3:26])=[N:15][N:14]=1>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](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[C:16]([CH2:25][CH3:26])=[N:15][N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109538273,5-Dichloro-4-methylpyridineHCID 183816451-Chloro-4-ethyl-6-methoxy-phthalazine

Product 1

HCID 99282611-(3,5-Dichloro-pyridin-4-ylmethyl)-4-ethyl-6-methoxy-phthalazineYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Operating substantially as described in example 5 starting from 3,5-dichloro-4-methyl-pyridine (1.75 g, 10.77 mmoles), dry DMF (20 ml), 60% NaH in oil (0.26 g, 10.77 mmoles) and 1-chloro-4-ethyl-6-methoxy-phthalazine (1.2 g, 5.39 mmoles), prepared as described in example 10, in DMF (25 ml), 0.66 g of the title compound were obtained (yield: 36%). m.p.: 136-138° C.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-396c93e6e15542618a563ee89cbac981
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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