Sodium hydride → 5-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazine

HRID 2300046Notes

Reaction equation

HRID 2300046 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:11])[C:9]=1[CH3:10].Cl[C:13]1[C:22]2[C:17](=[C:18]([O:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]=1>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:11])[C:9]=1[CH2:10][C:13]1[C:22]2[C:17](=[C:18]([O:25][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109538273,5-Dichloro-4-methylpyridineHCID 118219611-Chloro-5-cyclopentyloxy-6-methoxy-phthalazine

Product 1

HCID 98659165-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazineYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under stirring, 55% sodium hydride (3.73 g, 85.56 mmoles) was added to a solution, under nitrogen, of 3,5-dichloro-4-methyl-pyridine (13.86 g, 85.56 mmoles) in anhydrous DMF (100 ml). The mixture was kept under stirring for 1 hour then added with a solution of 1-chloro-5-cyclopentyloxy-6-methoxy-phthalazine (7.95 g, 28.52 mmoles), obtained as described in example 7, in anhydrous dimethylformamide (70 ml). After resting overnight, the mixture was quenched with water, diluted with water and extracted with ethyl acetate. The extract was washed with water and dried on sodium sulphate, then evaporated to dryness. The residue was flash chromatographed (eluent petrolatum/ethyl acetate 1:1) to give 6.58 g of the title compound (yield: 57%).

Workup

  1. stirringunder stirring for 1 hour
  2. customobtained
  3. customthe mixture was quenched with water
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried on sodium sulphate
  8. customevaporated to dryness
  9. customchromatographed (eluent petrolatum/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-c63977abe9034939a27ba13e61982bd1
Source dataset
uspto-grants-2002_12
Patent number
US06498160B2

Reaction notes

Loading…