Water → ethyl 4-(3-(methylamino)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882138Notes

Reaction equation

HRID 882138 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:16][NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.[Pd]>[CH3:16][NH:17][C:18]1[CH:19]=[C:20]([C:2]2[C:3]3[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 105611797H-Pyrrolo(2,3-d)pyrimidine-5-carboxylic acid, 4-chloro-, ethyl esterHCID 57976762N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 117703051ethyl 4-(3-(methylamino)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a nitrogen purged mixture of ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (300 mg, 1.33 mmol) and N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (465 mg, 1.99 mmol) in 2 M aqueous sodium carbonate solution (3.32 mL, 6.65 mmol) and dioxane (10 mL) was added SiliaCat® heterogeneous catalysts DPP-Pd (loading=0.28 mmol/g, 950 mg, 0.266 mmol). The reaction mixture was heated by microwave irradiation at 150° C. in a sealed microwave vessel for 30 minutes. Water (5 mL) was added to the reaction mixture and then the biphasic mixture was filtered. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (×3). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with 0-100% ethyl acetatehexane to give ethyl 4-(3-(methylamino)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C16H17N4O2[M+H]+: 297, found 297.

Workup

  1. customTo a nitrogen purged
  2. additionwas added SiliaCat® heterogeneous catalysts
  3. filtrationthe biphasic mixture was filtered
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (×3)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on silica eluting with 0-100% ethyl acetatehexane

Sources & evidence

ORD record
ord-2b1544bb00934467a80c807c7d23a20c
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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