Ammonium formate → HCID 22594101, compound

HRID 1760964Notes

Reaction equation

HRID 1760964 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:19]=2)=[CH:12][C:3]=1[NH:4][C:5]1[CH:10]=[C:9](Cl)[N:8]=[CH:7][N:6]=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:1][C:2]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:19]=2)=[CH:12][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22594108HCID 22594108, compound

Product 1

HCID 22594101HCID 22594101, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium-on-carbon (0.02 g) was added to a mixture of 4-[2-methyl-5-(3-morpholinobenzamido)anilino]-6-chloropyrimidine (0.169 g), ammonium formate (0.165 g) and ethanol (5 ml) and the resultant mixture was stirred and heated to reflux for 18 hours. The catalyst was removed by filtration and the filtrate was evaporated. The residue was partitioned between methylene chloride and water and the organic phase was washed with brine, dried over sodium sulphate and evaporated. There was thus obtained the title compound (0.145 g); NMR Spectrum: (DMSOd6) 2.23 (s, 3H), 3.24 (m, 4H), 3.83 (m, 4H), 6.68 (m, 1H), 7.2 (m, 1H), 7.3 (m, 1H), 7.43 (m, 2H), 7.5 (m, 1H), 7.61 (m, 1H), 7.88 (m, 1H), 8.28 (m, 1H), 8.57 (s, 1H), 9.06 (s, 1H), 10.18 (s, 1H); Mass Spectrum: M+H+ 390.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customThe catalyst was removed by filtration
  4. customthe filtrate was evaporated
  5. customThe residue was partitioned between methylene chloride and water
  6. washthe organic phase was washed with brine
  7. dry with materialdried over sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-f2ab103c20f84cb09e259905cda1b2c2
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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