1,4-Dioxane → HCID 23071563, compound

HRID 269831Notes

Reaction equation

O1CCOCC1.[NH2:7][C:8]([C:10]1[C:11]([NH:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[N:12][C:13]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)=[N:14][CH:15]=1)=[O:9].Cl.O1CCOCC1.C(=O)(O)[O-].[Na+]>O>[CH2:37]([NH:36][C:11]1[C:10]([C:8]([NH2:7])=[O:9])=[CH:15][N:14]=[C:13]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[N:12]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A 10 ml 1,4-dioxane solution of 738 mg of tert-butyl 4-(4-{[5-(aminocarbonyl)-4- (benzylamino)pyrimidin-2-yl]amino }phenyl)piperazin- 1 -carboxylate was mixed with 2.77 ml of 4 M hydrogen chloride/1,4-dioxane solution and 3 ml of water, followed by stirring at 90° C. for 2 hours. The reaction mixture was cooled down to room temperature, diluted with water, mixed with saturated sodium bicarbonate aqueous solution and then extracted with an ethyl acetate-THF mixed solution. After washing of the organic layer with saturated brine and subsequent evaporation of the solvent, the resulting solid was recrystallized (THF-ethanol) to obtain 413 mg of 4-benzylamino-2- {[4-(piperazin- 1 -yl)phenyl]amino}pyrimidine-5- carboxamide as ivory-colored crystals.

Workup

temperatureThe reaction mixture was cooled down to room temperature
extractionextracted with an ethyl acetate-THF mixed solution
washAfter washing of the organic layer with saturated brine and subsequent evaporation of the solvent
customthe resulting solid was recrystallized (THF-ethanol)

Sources & evidence

ORD record: ord-d9beba56a51143beb1ea2c3b3a7efcd0
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449456B2

Reaction notes

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