Water → HCID 22640034, compound

HRID 2415095Notes

Reaction equation

HRID 2415095 reaction equation
CC1(C)CC(=O)CC(=O)C1.C([O:14][C:15]1[CH:16]=[C:17]([CH:29]=[CH:30][C:31]=1[O:32][C:33]1[CH:34]=[CH:35][C:36]2[N:37]([C:39]([N+:42]([O-:44])=[O:43])=[CH:40][N:41]=2)[N:38]=1)[CH2:18][NH:19][C:20]1[C:25]([Cl:26])=[C:24]([CH3:27])[N:23]=[C:22]([CH3:28])[N:21]=1)C=C.O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:26][C:25]1[C:20]([NH:19][CH2:18][C:17]2[CH:16]=[C:15]([OH:14])[C:31]([O:32][C:33]3[CH:34]=[CH:35][C:36]4[N:37]([C:39]([N+:42]([O-:44])=[O:43])=[CH:40][N:41]=4)[N:38]=3)=[CH:30][CH:29]=2)=[N:21][C:22]([CH3:28])=[N:23][C:24]=1[CH3:27]

Participants

6

Reactant 3

HCID 962WaterHCID 31358DimedoneHCID 22640001HCID 22640001, compound

Product 1

HCID 22640034HCID 22640034, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

0.14 g (1.0 mmol) of dimedone and catalytic amount of tetrakis(triphenylphosphine)palladium(0) (12 mg) are added to a solution of 0.48 g (1.0 mmol) of [3-allyloxy-4-(3-nitro-imidazo[1,2-b]pyridazin-6-yloxy)-benzyl]-(5-chloro-2,6-dimethyl-pyrimidin-4-yl)-amine (from example A15) in 15 ml of dry toluene. The reaction mixture is refluxed under nitrogen for 1 h and then cooled to room temperature. The solution is poured into water (100 ml), extracted with ethyl acetate (4×100 ml) and the combined organic layers are dried with magnesium sulphate and concentrated in vacuo. The residue is crystallized from petroleum ether to give 0.44 g (50%) of the title compound as a beige powder of m.p. >114° C.

Workup

  1. temperatureThe reaction mixture is refluxed under nitrogen for 1 h
  2. extractionextracted with ethyl acetate (4×100 ml)
  3. dry with materialthe combined organic layers are dried with magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-7a654fcf27574252833dfd7f3c73e8f8
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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