Hydrochloric Acid → 1-Chloro-4-(4-pyrimidinylmethyl)phthalazine hydrochloride

HRID 1384145Notes

Reaction equation

HRID 1384145 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=O)[NH:10][N:9]=2)=[N:3][CH:2]=1.[ClH:19].P(Cl)(Cl)([Cl:22])=O>C(#N)C.O1CCOCC1>[ClH:22].[Cl:19][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][N:3]=2)=[N:9][N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 106813894-(4-pyrimidinylmethyl)-1(2H)-phthalazinone

Product 1

HCID 227419711-Chloro-4-(4-pyrimidinylmethyl)phthalazine hydrochloride

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

850 mg (3.57 mmol) 4-(4-pyrimidinylmethyl)-1 (2H)-phthalazinone in 15 ml acetonitrile is mixed with 1.78 ml (7.14 mmol) 4N HCl solution in dioxane and finally with 1.14 ml (12.5 mmol) phosphoryl chloride. After stirring for 36 h at 50° C., the red suspension is filtered and washed with acetonitrile: FAB MS (M−H)+=255. Further product is obtainable from the evaporated filtrate by distribution between dichioromethane and sat. NaHCO3 solution.

Workup

  1. filtrationthe red suspension is filtered
  2. washwashed with acetonitrile

Sources & evidence

ORD record
ord-3657c455d4b246f19d5a00e06e4fb19d
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Reaction notes

Loading…