Ethanol → HCID 58169392, compound

HRID 1484839Notes

Reaction equation

HRID 1484839 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25][C:26]#[N:27])=[CH:21][CH:20]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[NH4+].[Cl-].CCO>[Fe].O>[NH2:16][C:15]1[C:10]([NH:9][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:8][N:7]=2)=[N:11][C:12]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C:26]#[N:27])=[CH:23][CH:24]=2)=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 58169520HCID 58169520, compound

Product 1

HCID 58169392HCID 58169392, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a solid mixture of 2-(4-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-nitropyrimidin-2-yl)phenyl)acetonitrile 45 mg, 0.125 mmol, 1 equivalent) and NH4Cl (3.6 g, 1.375 mmol, 11 equiv) was added EtOH (4 ml) and H2O (2 mL). The reaction mixture was heated to reflux under nitrogen atmosphere and iron powder (25 mg, 0.438 mmol, 3.5 equiv.) was added. The resulting mixture was continued to reflux for 0.5 h. The mixture was filtered immediately with a hot filter under reduced pressure. EtOH and water were removed under reduce pressure. The residue was washed by water. The title compound 2-(4-(5-amino-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)phenyl) acetonitrile (Compound 92) (10 mg, 24.4%) was obtained. LC-MS (m/z)=332.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.71 (s, 2H), 0.93 (s, 2H), 1.92 (s, 1H), 3.83 (s, 2H), 5.30 (s, 2H), 6.21 (s, 2H), 7.04 (s, 1H), 7.21 (d, J=6.0 Hz, 1H), 7.53 (s, 1H), 7.70 (s, 1H), 8.30 (s, 1H), 9.78 (s, 1H), 12.03 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under nitrogen atmosphere
  3. temperatureto reflux for 0.5 h
  4. filtrationThe mixture was filtered immediately with
  5. filtrationa hot filter under reduced pressure
  6. customEtOH and water were removed
  7. washThe residue was washed by water

Sources & evidence

ORD record
ord-d1f2e1ea6ece41409c2c52e7d34d4b4d
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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