Ammonium Chloride → HCID 86713586, compound

HRID 2274205Notes

Reaction equation

HRID 2274205 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]#[C:14][C:15]1[CH:16]=[N:17][C:18]([NH:21][C:22]2[C:27]([N+:28]([O-])=O)=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:31])=[N:19][CH:20]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Cl:12][C:4]1[C:5]([O:10][CH3:11])=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[C:3]=1[C:13]#[C:14][C:15]1[CH:20]=[N:19][C:18]([NH:21][C:22]2[C:27]([NH2:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:31])=[N:17][CH:16]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86713587HCID 86713587, compound

Product 1

HCID 86713586HCID 86713586, compoundYield 40.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-((2,6-dichloro-3,5-dimethoxyphenyl)ethynyl)-N-(2-methyl-6-nitrophenyl)pyrimidin-2-amine (150 mg, 0.33 mmol), Iron (147 mg, 2.64 mmol) and ammonium chloride (214 mg, 3.96 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 (58 mg, 35%). MS (ES+) C21H18Cl2N4O2 requires: 429, 431. Found: 430, 432 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.90 (s, 1H), 8.55-8.44 (br, 2H), 6.97 (s, 1H), 6.89-6.86 (m, 1H), 6.57 (d, 1H, J=7.6 Hz), 6.44 (d, 1H, J=7.6 Hz), 4.75 (s, 2H), 3.94 (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-e265ba19de4d44b19cd92c463bbcaed2
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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