Tributylstannane → HCID 10181645, compound

HRID 861134Notes

Reaction equation

HRID 861134 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:22]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[N:24]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([NH:16][CH:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[CH:17]1([NH:16][C:15]2[N:10]3[N:9]=[C:8]([C:4]4[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=4)[C:22]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]5[CH2:31][CH2:32][CH2:33][CH2:34]5)[N:24]=4)=[C:11]3[CH:12]=[CH:13][CH:14]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 10142612HCID 10142612, compound

Product 1

HCID 10181645HCID 10181645, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(3-bromophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine (100 mg, 0.19 mmol) in toluene (10 mL) was added tributyltin hydride (112 mg, 0.39 mmol) and 2,2′-azobisisobutyronitrile (9.4 mg, 0.057 mmol). After heating at reflux for 4 hours, the reaction mixture was allowed to cool to room temperature. Concentration, followed by purification with flash chromatography (40:60 ethyl acetate:hexanes) gave N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-phenylpyrazolo[1,5-a]pyridin-7-amine as a yellow foam (39 mg, 46%). 1H NMR (CDCl3): δ 7.98 (d, 1H), 7.78 (d, 1H), 7.64 (m, 2H), 7.45 (m, 2H), 7.33–7.26 (m, 2H), 6.27 (d, 1H), 6.04 (m, 2H), 5.12 (d, 1H), 4.35 (m, 1H), 4.00 (m, 1H), 2.09–2.03 (m, 4H), 1.81–1.59 (m, 12H). MS m/z 439 (M+1).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 4 hours
  3. concentrationConcentration
  4. customfollowed by purification with flash chromatography (40:60 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-fe189e98c1184a668ae791a1061f5941
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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