Ammonia → HCID 59286598, compound

HRID 1876040Notes

Reaction equation

HRID 1876040 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[N:5]=[CH:4][N:3]=1.[NH3:13]>CO>[N:8]1([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH2:13])[CH:7]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27576124-Chloro-6-(1H-imidazol-1-yl)pyrimidine

Product 1

HCID 59286598HCID 59286598, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

4-Chloro-6-(1H-imidazol-1-yl)pyrimidine (4.0 g, 22.1 mmol) was split into two equal portions and separately placed into two sealed tubes with a solution of 7 N ammonia in methanol (40 mL). The tubes were sealed and heated at 65° C. for 20 h, then allowed to stand at room temperature for 3 days. The reactions were combined, concentrated and purified by flash chromatography on a 240 g silica gel cartridge with 40 to 100% EtOAc in hexane, then 0 to 50% MeOH in EtOAc to yield 6-(1H-imidazol-1-yl)pyrimidin-4-amine (1.43 g, 40%). LCMS: RT=0.39 min, MH+=162.1.

Workup

  1. customThe tubes were sealed
  2. concentrationconcentrated
  3. custompurified by flash chromatography on a 240 g silica gel cartridge with 40 to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-69f4442e2b4540a3b81a22fb92993363
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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