Ammonium Chloride → HCID 86713582, compound

HRID 2404040Notes

Reaction equation

HRID 2404040 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[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18]([NH:23][C:24]3[C:29]([N+:30]([O-])=O)=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:33])=[N:19][CH:20]=2)[N:15]([CH3:34])[C:14]1=[O:35].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:30][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:33])[C:24]=1[NH:23][C:18]1[N:17]=[C:16]2[N:15]([CH3:34])[C:14](=[O:35])[N:13]([C:3]3[C:2]([Cl:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=3[Cl:12])[CH2:22][C:21]2=[CH:20][N:19]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86713581HCID 86713581, compound

Product 1

HCID 86713582HCID 86713582, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-7-(2-methyl-6-nitrophenylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (290 mg, 0.56 mmol) in ethanol (10 mL) and water (2 mL) was stirred at 70° C. for 20 mins before iron powder (320 mg, 5.60 mmol) and ammonium chloride (250 mg, 2.79 mmol) were added. The reaction mixture was stirred at 70° C. for another 6 h. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated. The residue was dissolved by ethyl acetate (30 mL), washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by Prep-HPLC to give the title compound (27 mg, 10%) as a white solid. MS (ES+) C22H22Cl2N6O3 requires: 488, 490. found: 489, 491 [M+H]+. 1H-NMR (500 MHz, CDCl3) δ ppm 7.89 (s, 1H), 7.04 (t, 1H, J=8.0 Hz), 6.69 (d, 2H, J=7.5 Hz), 6.60 (s, 1H), 4.53 (s, 2H), 3.94 (s, 6H), 3.34 (s, 3H), 2.24 (s, 3H).

Workup

  1. additionwere added
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved by ethyl acetate (30 mL)
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-600f3b9bafff43959abacf467e776f11
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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