Ammonia → HCID 178426370, compound

HRID 524552Notes

Reaction equation

HRID 524552 reaction equation
N.C([N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][C:12]([N:26]1[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[N:27]1)=[N:13][C:14]=2[NH:18][C:19]1[CH:24]=[CH:23][C:22](Cl)=[CH:21][CH:20]=1)C1C=CC=CC=1.C(N1C2C(=NC(N3C(C)=CC(C)=N3)=NC=2NC2C=CC(Cl)=CC=2)N=C1)C1C=CC=CC=1.[Na].[Cl-].[NH4+].Cl>O>[CH3:32][C:28]1[CH:29]=[C:30]([CH3:31])[N:26]([C:12]2[N:11]=[C:10]3[C:15]([N:16]=[CH:17][NH:9]3)=[C:14]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:13]=2)[N:27]=1

Participants

8

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 24947114HCID 24947114, compoundHCID 59322267HCID 59322267, compound

Product 1

HCID 178426370HCID 178426370, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ammonia (75 mL) was condensed in a reaction flask equipped with a mechanical stirrer and cooled on an acetone dry-ice bath. A mixture of [9-benzyl-2-(3,5-dimethyl-pyrazol-1-yl)-9H-purin-6-yl]-(4-chloro-phenyl)-amine and [7-benzyl-2-(3,5-dimethyl-pyrazol-1-yl)-7H-purin-6-yl]-(4-chloro-phenyl)-amine (1.5 g, 3.49 mmol) was added. Under vigorous stirring small pieces of sodium (2 equiv) were added. When the addition was completed the reaction mixture turned dark blue. The mixture was stirred for 2 minutes followed by careful addition of ammonium chloride. The reaction mixture was allowed to warm to room temperature. Water and a small amount of concentrated hydrochloric acid were added. The resulting solid was collected by filtration, washed with water and ether and dried to give [2-(3,5-dimethyl-pyrazol-1-yl)-9H-purin-6-yl]-phenyl-amine (590 mg, 50%) as a white solid.

Workup

  1. customcondensed in a reaction flask
  2. customequipped with a mechanical stirrer
  3. temperaturecooled on an acetone dry-ice bath
  4. additionwas added
  5. additionWhen the addition
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water and ether
  8. customdried

Sources & evidence

ORD record
ord-1617658683c34e32be3b2e2adc6c232d
Source dataset
uspto-grants-2016_05
Patent number
US09340544B2

Reaction notes

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