Sodium Carbonate → HCID 45483929, compound

HRID 882184Notes

Reaction equation

HRID 882184 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[C:12]2[CH:19]=[CH:18][NH:17][C:13]=2[N:14]=[CH:15][N:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]1([C:11]2[C:12]3[CH:19]=[CH:18][NH:17][C:13]=3[N:14]=[CH:15][N:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 45483929HCID 45483929, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of phenylboronic acid (1.59 g, 13.0 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 6.51 mmol), sodium carbonate (1.38 g, 13.0 mmol), PdCl2(dppf) (113 mg, 0.138 mmol) in dioxane (20 mL) and water (5 mL) was purged with argon gas for 10 minutes and then heated by microwave irradiation at 150° C. for 1 hour. Brine was added to the reaction mixture and the organic layer was separated. The aqueous layer was then extracted with ethyl acetate (×3) and the organic layers were combined and dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was then purified by silica chromatography eluting with 10-80% ethyl acetatehexane to afford 4-phenyl-7H-pyrrolo[2,3-d]pyrimidine as a light brown solid. LRMS (ESI) calc'd for C12H9N3 [M]+: 195, found 195.

Workup

  1. customwas purged with argon gas for 10 minutes
  2. additionBrine was added to the reaction mixture
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was then extracted with ethyl acetate (×3)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was then purified by silica chromatography
  9. washeluting with 10-80% ethyl acetatehexane

Sources & evidence

ORD record
ord-15e2628c9d41414c838508940dd47742
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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