Phenylboronic Acid → HCID 58207181, compound

HRID 1409133Notes

Reaction equation

HRID 1409133 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH2:12])[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.[Cl-].[Na+].O.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:11][C:9]1[CH:10]=[C:6]2[N:5]=[C:4]([NH2:12])[CH:3]=[C:2]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:7]2[N:8]=1

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 442513077-Chloro-2-methylpyrazolo(1,5-a)pyrimidin-5-amine

Product 1

HCID 58207181HCID 58207181, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

7-Chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1J, 10 g, 55 mmol), phenylboronic acid (7.3 g, 60 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1.0 g, 1.4 mmol) were mixed in dioxane (120 ml) and saturated NaHCO3 (60 ml). The mixture was then heated at 100° C. for 4 hours. After cooling to room temperature, Brine was added and the mixture was extracted with EtOAc five times. Combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography (SiO2) to give 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 2.2 g, 18%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ=7.95-7.85 (m, 2H), 7.62-7.50 (m, 3H), 6.70 (s, 2H), 6.22 (s, 1H), 5.81 (s, 1H), 2.24 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc five times
  3. washCombined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-3247e98a65c8459eb7f2e2da8f8fd6d1
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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