Potassium Carbonate → HCID 44156896, compound

HRID 1801683Notes

Reaction equation

HRID 1801683 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][C:13]3[N:18]=[CH:17][N:16]=[C:15]4[N:19]([C:22]5[CH:27]=[CH:26][CH:25]=[C:24](I)[CH:23]=5)[N:20]=[CH:21][C:14]=34)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[C:29]([Si](C)(C)C)#[CH:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)(Cl)Cl.C(N(CC)CC)C.CN(C)C=O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][C:13]3[N:18]=[CH:17][N:16]=[C:15]4[N:19]([C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([C:29]#[CH:30])[CH:23]=5)[N:20]=[CH:21][C:14]=34)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 44184319HCID 44184319, compound

Product 1

HCID 44156896HCID 44156896, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
30 °C

Procedure

50 ml of dimethylformamide was charged into a 250 ml 4 necked round bottom flask, connected to a mechanical stirrer, thermometer socket, condenser, addition funnel and nitrogen gas bubbler. 10.0 g (20.60 mmol) of (2,3-Dihydro-benzo[1,4]dioxin-6-yl methyl)-[1-(3-iodo-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amine (Compound No. 25), 14.50 g (0.146 mol) of ethynyl trimethyl silane, 46.0 mg of palladium acetate hexakis(acetato)tri palladium (II) 108.0 mg of triphenyl phosphine and 20.6 ml of triethyl amine were charged. Maintained the mass temperature at 25-35° C. for 30-45 min. Reaction mass temperature was raised to 80-85° C. Maintained the mass temperature at 80-85° C. for 4 hours. Reaction mass temperature was cooled to 50-55° C. and maintained for 2 hours. Reaction mass temperature was cooled to 25-30° C. and maintained for overnight under stirring. Solvent was completely distilled off under vacuum. The crude oil present was dissolved in 160 ml of water and compound was extracted with 300 ml of chloroform. Organic layer was dried with sodium sulphate. Sodium sulphate was filtered and washed the sodium sulphate with 50 ml of chloroform. Distilled off chloroform completely under vacuum. 9.50 g Of crude oil (Compound No. 13) was obtained. Compound was characterized by Mass spectrum [455 (M+1)]. 9.0 g of crude oil was dissolved in 85 ml of methanol and 85 ml of chloroform mixture. 11.30 g of potassium carbonate was added. Maintained the mass temperature at 25-35° C. for 14 hours. Distilled of the solvent completely under vacuum. 7.50 g Of crude oil was obtained. Crude oil was purified by the column chromatography with hexane and ethyl acetate mixture as mobile phase. Obtained 3.60 g (yield; 45.70% by theory) of product.

Workup

  1. customconnected to a mechanical stirrer
  2. additionthermometer socket, condenser, addition funnel and nitrogen gas bubbler
  3. customReaction mass temperature
  4. temperaturewas raised to 80-85° C
  5. temperatureMaintained the mass temperature at 80-85° C. for 4 hours
  6. customReaction mass temperature
  7. temperaturewas cooled to 50-55° C.
  8. temperaturemaintained for 2 hours
  9. customReaction mass temperature
  10. temperaturewas cooled to 25-30° C.
  11. temperaturemaintained for overnight
  12. distillationSolvent was completely distilled off under vacuum
  13. dissolutionThe crude oil present was dissolved in 160 ml of water
  14. extractioncompound was extracted with 300 ml of chloroform
  15. dry with materialOrganic layer was dried with sodium sulphate
  16. filtrationSodium sulphate was filtered
  17. washwashed the sodium sulphate with 50 ml of chloroform
  18. distillationDistilled off chloroform completely under vacuum
  19. custom9.50 g Of crude oil (Compound No. 13) was obtained
  20. temperatureMaintained the mass temperature at 25-35° C. for 14 hours
  21. distillationDistilled of the solvent completely under vacuum

Sources & evidence

ORD record
ord-fd06b2157b504b928323ecf35a341414
Source dataset
uspto-grants-2013_01
Patent number
US08349847B2

Reaction notes

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