Ammonium Chloride → HCID 86713569, compound

HRID 2274185Notes

Reaction equation

HRID 2274185 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:31]=[N:30][C:14]3[N:15]=[C:16]([NH:19][C:20]4[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:29])[N:17]=[CH:18][C:13]=3[CH:12]=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]2[CH:31]=[N:30][C:14]3[N:15]=[C:16]([NH:19][C:20]4[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:29])[N:17]=[CH:18][C:13]=3[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86713568HCID 86713568, compound

Product 1

HCID 86713569HCID 86713569, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-(3,5-dimethoxyphenyl)-N-(2-methyl-6-nitrophenyl)pyrido[2,3-d]pyrimidin-2-amine (100 mg, 0.24 mmol) in ethanol (5 mL) and water (5 mL) was added iron powder (110 mg, 1.92 mmol) and ammonium chloride (100 mg, 1.920 mmol). The mixture was stirred at 100° C. for 1 hour, cooled to RT, filtered and concentrated. The residue was purified by Preparative HPLC to afford N1-(6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-yl)-6-methylbenzene-1,2-diamine (29.5 mg, 32%) as a yellow solid. MS (ES+) C22H21N5O2 requires: 387. Found: 388 [M+H]+; 1H-NMR (500 MHz, DMSO-d6) δ ppm 9.30, 9.21 (br, br, 2H), 8.95 (s, 1H), 8.60 (d, 1H, J=3.0 Hz), 6.96-6.92 (m, 3H), 6.63 (d, 1H, J=5.5 Hz), 6.55 (t, 1H, J=2.0 Hz), 6.50-6.48 (m, 1H), 4.79 (s, 2H), 3.84 (s, 6H), 2.08 (s, 3H).

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by Preparative HPLC

Sources & evidence

ORD record
ord-16f6eba9679c477a8e606c814484f738
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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