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2-(Tributylstannyl)pyridine → HCID 11530806, compound

HRID 2099226
Notes
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Reaction equation

HRID 2099226 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C:11]1[CH:12]=[C:13]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:14]([NH:16][CH:17]1[CH2:19][CH2:18]1)=[O:15].C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)CCC>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:17]1([NH:16][C:14](=[O:15])[C:13]2[CH:20]=[CH:21][C:22]([CH3:23])=[C:11]([N:6]3[CH:5]=[N:4][C:3]4[C:7]3=[N:8][CH:9]=[N:10][C:2]=4[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[CH:12]=2)[CH2:19][CH2:18]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 57794379HCID 57794379, compound

Product 1

HCID 11530806HCID 11530806, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 3-(6-chloro-purin-9-yl)-N-cyclopropyl-4-methyl-benzamide (16 mg, 0.049 mmol), Pd(PPh3)4 (5.7 mg, 0.0049 mmol) and the 2-tributylstannanyl-pyridine (36 mg, 0.098 mmol) was suspended in DMF (0.25 ml). The mixture was heated with microwave at 160° C. for 10 minutes. The mixture was purified by HPLC to give the desired product as a white solid (16 mg, 0.043 mmol, 88%). HPLC tR=1.59 min; MS m/z 371 [M+H]+.

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-5b5e48d7370b4f829eeb3c260f44eea8
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07569571B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes