Ammonium formate → HCID 59216019, compound

HRID 2245224Notes

Reaction equation

HRID 2245224 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[N:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1.C([O-])=O.[NH4+]>[Pd]>[CH3:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:11])[N:5]=[C:4]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[N:3]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 59216020HCID 59216020, compound

Product 1

HCID 59216019HCID 59216019, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
150 °C

Procedure

The suspension of 4-(4,6-dimethyl-5-nitropyrimidin-2-yl)-morpholine (2.2 g, 9.23 mmol), 5% palladium on activated carbon (50% wet, 1.09 g), ammonium formate (8.76 g) was sealed in the Emrys process vial and heated at 150° C. under microwave irradiation for 2 min. The reaction mixture was filtered and evaporated. The residue was treated with ethyl acetate and filtered to give 1.62 g of orange crystalline product after evaporation in vacuo. Yield 84%. LC-MS (m/z) 208.9 (MH+); tR=0.44. 1H NMR (500 MHz, DMSO-d6): 2.2 (s, 6H), 3.44 (m, 4H), 3.62 (m, 4H), 4.19 (br, 2H, NH2).

Workup

  1. customwas sealed in the Emrys process vial
  2. filtrationThe reaction mixture was filtered
  3. customevaporated
  4. additionThe residue was treated with ethyl acetate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-96492a693e7b4fe39630ddfdd660ba4a
Source dataset
uspto-grants-2010_03
Patent number
US07683058B2

Reaction notes

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