Hydrochloric Acid → HCID 178420152, compound

HRID 2274494Notes

Reaction equation

HRID 2274494 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[NH:17][N:16]=[N:15][N:14]=3)=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 140043942-Phenylpyrimidine-5-carbonitrile

Product 1

HCID 178420152HCID 178420152, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture consisting of 2-phenylpyrimidine-5-carbonitrile (200 mg, 1.10 mmol), sodium azide (80 mg, 1.2 mmol) and ammonium chloride (66 mg, 1.2 mmol) in DMF (3 mL) was stirred at 100° C. for 24 hours. The reaction mixture was allowed to cool to room temperature. Upon addition of 1N hydrochloric acid (3 mL), a white solid precipitated. The precipitate was isolated by filtration and recrystallized from ethanol to afford the title compound as a white solid (123 mg, 50% yield); melting point 237° C.; 1H-NMR (400 MHz; DMSO-d6) δ 9.51 (s, 2H), 8.51-8.53 (m, 2H), 7.61-7.65 (m, 3H); LC/MS (ESI+) m/z 225; H-PGDS FPBA IC50: 2.5 μM.

Workup

  1. temperatureto cool to room temperature
  2. customa white solid precipitated
  3. customThe precipitate was isolated by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c6e59d60c7004e589ca324c479af41ce
Source dataset
uspto-grants-2015_09
Patent number
US09126973B2

Reaction notes

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