Ammonium formate → HCID 23505787, compound

HRID 1884611Notes

Reaction equation

HRID 1884611 reaction equation
[N+:1]([C:4]1[C:5]([C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)=[N:6][C:7]([O:10][C:11]2[N:16]=[C:15]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[C:14]([N+:27]([O-])=O)=[CH:13][N:12]=2)=[N:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>CCOC(C)=O.CCO.[Pd]>[NH2:27][C:14]1[C:15]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[N:16][C:11]([O:10][C:7]2[N:6]=[C:5]([C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][CH:31]=3)[C:4]([NH2:1])=[CH:9][N:8]=2)=[N:12][CH:13]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 86587096Nitronaphthyl-pyrimidinyl ether

Product 1

HCID 23505787HCID 23505787, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude nitronaphthyl-pyrimidinyl ether from above (459 mg, 1.42 mmol, 1 equiv.) was taken up in 35 mL EtOAc and 35 mL EtOH. Ammonium formate was added (537 mg, 8.52 mmol, 6 equiv.) as well as 400 mg of 10% palladium-on-carbon. The reaction mixture was heated to a gentle reflux for one h, cooled back to room temperature, filtered through diatomaceous earth and the volatiles were removed in vacuo. The crude product was purified by chromatography on SiO2, eluting with 20-40% EtOAc in hexanes. The desired aminonaphthyl-pyrimidyl ether was isolated as a yellow foam (176 mg, 0.6 mmol, 42% for 2 steps).

Workup

  1. temperatureThe reaction mixture was heated to
  2. temperaturea gentle reflux for one h
  3. filtrationfiltered through diatomaceous earth
  4. customthe volatiles were removed in vacuo
  5. customThe crude product was purified by chromatography on SiO2
  6. washeluting with 20-40% EtOAc in hexanes

Sources & evidence

ORD record
ord-00bcce98888145dc80ecbdc4cb7bcb28
Source dataset
uspto-grants-2004_07
Patent number
US06765009B2

Reaction notes

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