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Ammonium Chloride → 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-ethylpyrimidin-2-amine

HRID 45884
Notes
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Reaction equation

HRID 45884 reaction equation
[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([C:10]2[C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=3)=[N:12][N:13]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:14]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2].[Cl-].[NH4+]>O1CCOCC1.O.[Zn]>[NH2:30][C:26]1[CH:25]=[C:24]([C:11]2[C:10]([C:8]3[CH:7]=[CH:6][N:5]=[C:4]([NH:3][CH2:1][CH3:2])[N:9]=3)=[CH:14][N:13]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[N:12]=2)[CH:29]=[CH:28][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67184314N-ethyl-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyrimidin-2-amine

Product 1

HCID 671848314-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-ethylpyrimidin-2-amineYield 93.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962
Water
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

391 mg (0.91 mmol) of N-ethyl-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyrimidin-2-amine were dissolved in a mixture of 20 ml of dioxane and 4 ml of water. 239 mg (3.64 mmol) of metallic zinc and 485 mg (9.1 mmol) of ammonium chloride were then added to the resulting solution. The reaction was carried out at 100° C. under stirring for 5 hours. The suspension was then filtered through a celite pad and the filtrate evaporated in vacuo. The residue was partitioned between dichloromethane and aqueous sodium hydrogenocarbonate and the organic layer dried over sodium sulphate and concentrated to give a crude purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 7/3), affording 340 mg (93%) of the title compound.

Workup

  1. customwas carried out at 100° C.
  2. filtrationThe suspension was then filtered through a celite pad
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was partitioned between dichloromethane and aqueous sodium hydrogenocarbonate
  5. dry with materialthe organic layer dried over sodium sulphate
  6. concentrationconcentrated
  7. customto give a crude
  8. custompurified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 7/3)

Sources & evidence

ORD record
ord-9ec0b154d1f64f3b860ac0fef64a2b2c
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541575B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes