Sodium Carbonate → ethyl 4-(3-aminophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882132Notes

Reaction equation

HRID 882132 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:8]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:4]=2[N:5]=[CH:6][N:7]=1.O.[NH2:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:25][C:26]1[CH:31]=[C:30]([C:2]2[C:3]3[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:8]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:4]=3[N:5]=[CH:6][N:7]=2)[CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 143894233-Aminophenylboronic acid monohydrateHCID 89616022ethyl 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Product 1

HCID 89630036ethyl 4-(3-aminophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of ethyl 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (1.00 g, 2.81 mmol), 3-aminophenylboronic acid monohydrate (577 mg, 4.21 mmol), 2 M aqueous sodium carbonate (893 mg, 8.43 mmol), and tetrakis(triphenylphosphine)palladium(0) (649 mg, 0.562 mmol) in dioxane (10 mL) and water (2 mL) was purged with argon. The reaction vessel was sealed in a microwave vial and the reaction mixture heated at 95° C. for 2 hours. The resulting mixture was filtered through Celite. Water (10 mL) was added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (×3). The combined organic layers were washed with brine (15 mL), 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 afford ethyl 4-(3-aminophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C21H29N4O3Si [M+H]+: 413, found 413.

Workup

  1. customwas purged with argon
  2. customThe reaction vessel was sealed in a microwave vial
  3. filtrationThe resulting mixture was filtered through Celite
  4. additionWater (10 mL) was added
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (×3)
  7. washThe combined organic layers were washed with brine (15 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by chromatography on silica eluting with 0-100% ethyl acetatehexane

Sources & evidence

ORD record
ord-d55790e608b1448099ca295c854508e7
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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