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Hydrochloric Acid → 2-{6-[2-(Dimethylamino)ethoxy]pyrimidin-4-yl}-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one hydrochloride

HRID 37901
Notes
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Reaction equation

HRID 37901 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:8])[CH2:5][CH2:6][OH:7].[Cl:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]([N:16]2[C:20](=[O:21])[C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][NH:17]2)[CH:11]=1.Cl>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[ClH:9].[CH3:3][N:4]([CH3:8])[CH2:5][CH2:6][O:7][C:10]1[N:15]=[CH:14][N:13]=[C:12]([N:16]2[C:20](=[O:21])[C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][NH:17]2)[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 866723282-(6-Chloropyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

Product 1

HCID 708728552-{6-[2-(Dimethylamino)ethoxy]pyrimidin-4-yl}-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one hydrochloride

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalyst
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

99 mg (0.4 mmol, 60% in mineral oil) of sodium hydride are added to a solution of 35 μl (31 mg, 0.4 mmol) of N,N-dimethylethanolamine and 2 ml of anhydrous THF, and the mixture is stirred for 10 min 100 mg (0.4 mmol) of the compound from Example 23, suspended in 3 ml of anhydrous THF, and 6 mg (0.02 mmol) of tetra-n-butylammonium iodide are added, and the mixture is stirred at RT for 16 h. 1 N hydrochloric acid and water are then added, the mixture is concentrated on a rotary evaporator and the residue is stirred in methanol. The precipitated solid is filtered off, and the filtrate is concentrated under reduced pressure. The filter residue is stirred in diethyl ether, the precipitate is filtered off and the filter residue is purified further by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid). The resulting formate salt of the target compound is converted into the hydrochloride by addition of 2 ml 1 M hydrochloric acid and reconcentration.

Workup

  1. concentrationthe mixture is concentrated on a rotary evaporator
  2. stirringthe residue is stirred in methanol
  3. filtrationThe precipitated solid is filtered off
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. stirringThe filter residue is stirred in diethyl ether
  6. filtrationthe precipitate is filtered off
  7. customthe filter residue is purified further by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)
  8. additionThe resulting formate salt of the target compound is converted into the hydrochloride by addition of 2 ml 1 M hydrochloric acid and reconcentration

Sources & evidence

ORD record
ord-c39be85efd1e4e9797d004187cae004c
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524699B2

Reaction notes

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