Sodium Bicarbonate → HCID 58174067, compound

HRID 339798Notes

Reaction equation

HRID 339798 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][N:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][N:23]=1.C([O-])(O)=O.[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[F:21][C:22]1[N:23]=[CH:24][C:25]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]3[C:20]4[C:15](=[N:16][CH:17]=[CH:18][N:19]=4)[N:14]=[CH:13][N:12]=3)=[CH:4][CH:3]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 58174271HCID 58174271, compound

Product 1

HCID 58174067HCID 58174067, compoundYield 9.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a round bottom flask was added [2-(4-bromophenyl)-ethyl]-pteridin-4-yl-amine (200 mg, 0.61 mmol), 2-fluoro-5-pyridineboronic acid (102 mg, 0.73 mmol), NaHCO3 (102 mg, 1.21 mmol), PdCl2(PPh3)2 (213 mg) and 50% aqueous ethylene glycol dimethyl ether (DME; 3.0 mL). The reaction was heated to reflux for 4.5 h, after which the reaction was cooled and the resulting orange precipitate filtered. The filtered material was washed with EtOAc and the filtrate washed with H2O. The organic fractions were pooled and concentrated in vacuo. The residue (229 mg) was purified by preparative RP-HPLC to afford {2-[4-(6-fluoropyridin-3-yl)-phenyl]-ethyl}-pteridin-4-yl-amine (20 mg) as an orange solid: mp 184-186° C.; EIMS m/z 346 ([M]+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4.5 h
  3. temperatureafter which the reaction was cooled
  4. filtrationthe resulting orange precipitate filtered
  5. washThe filtered material was washed with EtOAc
  6. washthe filtrate washed with H2O
  7. concentrationconcentrated in vacuo
  8. customThe residue (229 mg) was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-d5d57085b75e4c89a7655e558e7897b4
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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