Sodium Carbonate → N-(4-{2-[(4-morpholin-4-ylphenyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}phenyl)acetamide

HRID 2091969Notes

Reaction equation

HRID 2091969 reaction equation
Br[C:2]1[C:3]2[CH:23]=[CH:22][NH:21][C:4]=2[N:5]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[N:7]=1.[C:24]([NH:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)(=[O:26])[CH3:25].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[N:15]1([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6]3[N:7]=[C:2]([C:31]4[CH:32]=[CH:33][C:28]([NH:27][C:24](=[O:26])[CH3:25])=[CH:29][CH:30]=4)[C:3]4[CH:23]=[CH:22][NH:21][C:4]=4[N:5]=3)=[CH:10][CH:11]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27346574-Acetamidophenylboronic acidHCID 57991309HCID 57991309, compound

Product 1

HCID 57990878N-(4-{2-[(4-morpholin-4-ylphenyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-bromo-N-(4-morpholin-4-ylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine B (284 mg, 0.76 mmol), 4-acetoamidophenylboronic acid C (340 mg, 2.5 eq), tetrakis(triphenyl-phosphine)palladium(0) (120 mg, 0.1 mmol), and 1M Na2CO3 (1 ml, 1 mmol) in 1,4-dioxane (15 ml) was heated at reflux overnight. The mixture was cooled, extracted with 3N HCl. The aqueous layer was washed with ethylacetate, and then basified with 6N NaOH. The solid was filtered, and the crude product was purified by preparative HPLC to give the product N-(4-{2-[(4-morpholin-4-ylphenyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}phenyl)acetamide D (0.8 mg, 0.25%) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. extractionextracted with 3N HCl
  5. washThe aqueous layer was washed with ethylacetate
  6. filtrationThe solid was filtered
  7. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-100c470571714db0befbf0b900dc075c
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

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