Potassium Carbonate → 5-(2-methoxyphenyl)-4-phenyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 882188Notes

Reaction equation

HRID 882188 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:4]=2[N:5]=[CH:6][N:7]=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CCOC(C)=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(Cl)Cl>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:3]2[C:2]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:7][CH:6]=[N:5][C:4]=2[N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:9]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 896300714-chloro-5-(2-methoxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 896301495-(2-methoxyphenyl)-4-phenyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a nitrogen gas purged mixture of 4-chloro-5-(2-methoxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (50 mg, 0.13 mmol) and phenyl boronic acid (23.5 mg, 0.192 mmol) in 2 M potassium carbonate (0.192 mL, 0.385 mmol) and tetrahydrofuran (1.0 mL) was added PdCl2(dppf)-CH2Cl2 (10 mg, 0.013 mmol). The reaction was sealed and heated to 120° C. for 20 minutes. Upon cooling, the reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate and brine. The organic layer was then dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica chromatography eluting with 1-20% ethyl acetate/hexanes to afford 5-(2-methoxyphenyl)-4-phenyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. LRMS (ESI) calcd for C25H30N3O2Si [M+H]+: 432, found 432.

Workup

  1. customTo a nitrogen gas purged
  2. customThe reaction was sealed
  3. temperatureUpon cooling
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialThe organic layer was then dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica chromatography
  9. washeluting with 1-20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4e21611589ec4001b3cb9d30cbec60aa
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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