Tetrahydrofuran → HCID 57747428, compound

HRID 386643Notes

Reaction equation

HRID 386643 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][C:10]2[C:11]3[N:34]([CH3:35])[CH:33]=[CH:32][C:12]=3[N:13]=[C:14]([N:16]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:15]=2)=[C:4]([CH3:36])[CH:3]=1.[N:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.C1COCC1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.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>[CH3:36][C:4]1[CH:3]=[C:2]([C:40]2[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[S:9][C:10]1[C:11]2[N:34]([CH3:35])[CH:33]=[CH:32][C:12]=2[N:13]=[C:14]([N:16]([C:24]2[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=2)[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[N:15]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 57747383HCID 57747383, compound

Product 1

HCID 57747428HCID 57747428, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 4-(4-bromo-2,6-dimethylphenylthio)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl(4-cyanophenyl)carbamate (0.729 mmol) is combined with pyridine-4-boronic acid (1.46 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.0729 mmol) in a two dram vial. The vial is sealed and flushed with argon. Degassed THF (5.0 mL) and aqueous Na2CO3 (2 M, 1.5 mL, 3.0 mmol) are injected, and the mixture agitated on a shaker at 80° C. for 10 h. The mixture is diluted with ethyl acetate and extracted with aqueous Na2CO3 (0.5 M, ×2). The organic layer is collected, concentrated, and the residue purified by chromatography (SiO2, 1:4 hexanes/EtOAc).

Workup

  1. customThe vial is sealed
  2. customflushed with argon
  3. extractionextracted with aqueous Na2CO3 (0.5 M, ×2)
  4. customThe organic layer is collected
  5. concentrationconcentrated
  6. customthe residue purified by chromatography (SiO2, 1:4 hexanes/EtOAc)

Sources & evidence

ORD record
ord-03dffe62fa124f1cb7a8d9101e30a370
Source dataset
uspto-grants-2013_02
Patent number
US08372852B2

Reaction notes

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