Ammonium Chloride → HCID 86713585, compound

HRID 2404043Notes

Reaction equation

HRID 2404043 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]#[C:12][C:13]2[CH:14]=[N:15][C:16]([NH:19][C:20]3[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:29])=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]#[C:12][C:13]2[CH:14]=[N:15][C:16]([NH:19][C:20]3[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:29])=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86713584HCID 86713584, compound

Product 1

HCID 86713585HCID 86713585, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-((3,5-dimethoxyphenyl)ethynyl)-N-(2-methyl-6-nitrophenyl)pyrimidin-2-amine (150 mg, 0.38 mmol), Iron (171 mg, 3.04 mmol) and ammonium chloride (246 mg, 4.56 mmol) in ethanol (20 mL) and water (2 mL) was stirred at 85° C. for 1 h. LCMS showed the reaction was completed. The reaction was cooled to RT, and the solid was filtered off. The filtrate was concentrated, and the residue was purified by Prep-HPLC to afford the title compound as a white solid (55 mg, 44%). MS (ES+) C21H20N4O2 requires: 360. found: 361 [M+H]+. 1H-NMR (500 MHz, DMSO-d6) δ ppm 8.76 (s, 1H), 8.50-8.46 (br, 2H), 6.88 (t, 1H, J=7.0 Hz), 6.66 (s, 2H), 6.57 (d, 1H, J=7.5 Hz), 6.54 (s, 1H), 6.44 (d, 1H, J=6.5 Hz), 4.74 (s, 2H), 3.76 (s, 6H), 2.01 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to RT
  2. filtrationthe solid was filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-13ef5a7fd79f4c17bfe1d13bfef2867e
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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