Toluene → 4-Chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine

HRID 611531Notes

Reaction equation

HRID 611531 reaction equation
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[N+:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([O-:17])=[O:16].C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O.C(O)C>[Cl:1][C:2]1[C:3]2[C:10]([C:21]3[CH:22]=[CH:23][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=3)=[CH:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27735524-Nitrophenylboronic acidHCID 195974264-Chloro-5-iodo-7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 195974814-Chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 4-chloro-5-iodo-7-isopropylpyrrolo[2,3-d]pyrimidine (0.57 g), 4-nitrophenylboronic acid (0.30 g), bis(triphenylphosphine)palladium (II) chloride (0.126 g), toluene (15 ml), ethanol (2 ml), water (4 ml) and sodium bicarbonate (0.45 g) was heated under nitrogen at 105° C. for 8 hours. The mixture was cooled to ambient temperature and then partitioned between brine (50 ml) and ethyl acetate (50 ml). The aqueous layer was further extracted with ethyl acetate and the combined ethyl acetate extracts were washed with water, dried, filtered and evaporated to leave a solid which was purified by flash column chromatography on silica using cyclohexane with increasing amounts of ethyl acetate as the mobile phase to give 4-chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between brine (50 ml) and ethyl acetate (50 ml)
  3. extractionThe aqueous layer was further extracted with ethyl acetate
  4. washthe combined ethyl acetate extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a solid which
  9. customwas purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-e4bd162e3c0b4c23a0239173e397c33f
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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