Tributylstannane → HCID 10205591, compound

HRID 1373844Notes

Reaction equation

HRID 1373844 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)[N:25]=3)=[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:11]3[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].N(C(C)(C)C#N)=NC(C)(C)C#N.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]4[CH2:32][CH2:33][CH2:34][CH2:35]4)[N:25]=3)=[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([NH:17][CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22]4)[N:11]3[N:10]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 10187569HCID 10187569, compound

Product 1

HCID 10205591HCID 10205591, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(3-bromo-4-chlorophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-α]pyridin-7-amine (200 mg, 0.36 mmol) in toluene (15 mL) was added 2,2′-azobisisobutyronitril (30 mg, 0.18 mmol) and tributyltin hydride (282 mg, 97 mmol). After heated at reflux for 24 hours, the reaction mixture was cooled to room temperature. Concentration followed by purification with flash chromatograph (30:70 ethyl acetate/hexanes) gave 2-(4-chlorophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-α]pyridin-7-amine as a white foam. 1H NMR (CDCl3): δ 8.02 (d, 1H), 7.72 (m, 1H), 7.60 (d, 2H), 7.41 (d, 2H), 7.35 (m, 1H), 6.31 (d, 1H), 6.03 (m, 2H), 5.17 (br, 1H), 4.32 (m, 1H), 4.00 (m, 1H), 2.18–2.05 (m, 4H), 1.82–1.50 (m, 12H). MS m/z 474 (M+1).

Workup

  1. temperatureAfter heated
  2. temperatureat reflux for 24 hours
  3. concentrationConcentration
  4. customfollowed by purification with flash chromatograph (30:70 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4a3cb7f2f4fa427daf992b171eb3b8f0
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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