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Ammonium Chloride → HCID 86713570, compound

HRID 2404025
Notes
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Reaction equation

HRID 2404025 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]1[CH:33]=[N:32][C:16]2[N:17]=[C:18]([NH:21][C:22]3[C:27]([N+:28]([O-])=O)=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:31])[N:19]=[CH:20][C:15]=2[CH:14]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[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]1[CH:33]=[N:32][C:16]2[N:17]=[C:18]([NH:21][C:22]3[C:27]([NH2:28])=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:31])[N:19]=[CH:20][C:15]=2[CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86713571HCID 86713571, compound

Product 1

HCID 86713570HCID 86713570, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962
Water
Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-N-(2-methyl-6-nitrophenyl)pyrido[2,3-d]pyrimidin-2-amine (80 mg, 0.168 mmol) in ethanol (4 mL) and water (4 mL) was added iron powder (75 mg, 1.344 mmol) and ammonium chloride (74 mg, 1.344 mmol). The mixture was stirred at 100° C. for 2 hrs, cooled to RT, filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1) to afford N1-(6-(2,6-dichloro-3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-yl)-6-methylbenzene-1,2-diamine (40 mg, 53%) as a yellow solid. MS (ES+) C22H19Cl2N5O2 requires: 455, 457. found: 456, 458 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.33 (br. s., 1H), 9.01 (s, 1H), 9.65 (br. s., 1H), 8.23 (s, 1H), 7.05 (s, 1H), 6.93 (br. s., 1H), 6.64-6.63 (m, 1H), 6.50-6.49 (m, 1H), 4.80 (s, 2H), 3.99 (s, 6H), 2.09 (s, 3H).

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1)

Sources & evidence

ORD record
ord-9db996bee0ff47fb97fb2926f0830784
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08802697B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes