Methane → HCID 21109811, compound

HRID 1766202Notes

Reaction equation

HRID 1766202 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11](=[O:33])/[CH:12]=[CH:13]/[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][C:23]3=[O:32])[CH2:18][CH2:17]2)=[O:15])[CH:5]=[CH:6][C:7]=1[N:8]([CH3:10])[CH3:9].C.[H][H].[K+].[Br-]>C(O)C.C1COCC1.[Pt]>[Cl:1][C:2]1[CH:3]=[C:4]([C:11](=[O:33])[CH2:12][CH2:13][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][C:23]3=[O:32])[CH2:18][CH2:17]2)=[O:15])[CH:5]=[CH:6][C:7]=1[N:8]([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 297MethaneHCID 253877Potassium BromideHCID 21109728HCID 21109728, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21109811HCID 21109811, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 1.05 g (2.248 mmol) of (E)-3-{1-[4-(3-chloro-4-dimethylaminophenyl)-1,4-dioxo-2-buten-1-yl]-4-piperidinyl}-3,4-dihydro-2(1H)-quinazolinone (Item no. 104) in 110 ml of an ethanol-THF mixture (10/1 v/v) was hydrogenated at ambient temperature in the presence of 0.5 g of platinum on active charcoal until the uptake of hydrogen had ended. The mixture was freed from catalyst and solvent and purified by chromatography on silica gel using dichloromethane/methanol/conc. ammonia (95/5/0.3 v/v/v) as eluant. 0.36 g (34% of theoretical) of a colourless substance were obtained, Rf 0.31 (El A). IR (KBr): 1672, 1660 (C═O) MS: M+=468/470 (Cl)

Workup

  1. custompurified by chromatography on silica gel
  2. custom0.36 g (34% of theoretical) of a colourless substance were obtained

Sources & evidence

ORD record
ord-6b397f3645ce4e6c9251705c64f1964b
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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