Cesium carbonate → N-(3-(2-(6-(4-Ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

HRID 2042212Notes

Reaction equation

HRID 2042212 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36]2[N:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)[CH3:29].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:28]([N:30]1[CH2:31][CH2:32][N:33]([C:36]2[N:41]=[CH:40][C:39]([NH:42][C:2]3[N:3]=[CH:4][C:5]4[S:10][CH:9]=[C:8]([C:11]5[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=5)[C:6]=4[N:7]=3)=[CH:38][CH:37]=2)[CH2:34][CH2:35]1)[CH3:29]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 91616746-(4-Ethylpiperazin-1-yl)pyridin-3-amineHCID 86673215N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

Product 1

HCID 51347359N-(3-(2-(6-(4-Ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamideYield 53.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide (20 mg, 0.059 mmol) was dissolved in dioxane (1 mL) and then cesium carbonate (58 mg, 0.18 mmol) and 6-(4-ethylpiperazin-1-yl)pyridin-3-amine (18 mg, 0.088 mmol) were added. After flowing nitrogen gas to the reaction mixture for 10 minutes, Pd(OAc)2 (1 mg, 0.1 mmol) and Xantphos (4 mg, 0.12 mmol) were added. The reaction mixture was stirred at 120° C. for 6 hours and filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was dried with magnesium sulfate and concentrated by filtering with celite. Purification by chromatography (5% methanol/dichloromethane) yielded the target compound (16 mg, 53% yield).

Workup

  1. customfor 10 minutes
  2. filtrationfiltered with celite
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated
  7. filtrationby filtering with celite
  8. customPurification by chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-e0adc1e09bfc4e7f950a9c97ea28c021
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

Loading…