Tributylvinyltin → HCID 59924954, compound

HRID 2300814Notes

Reaction equation

HRID 2300814 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23](I)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:26]([Sn](C=C)(CCCC)CCCC)[CH2:27]CC>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>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([CH:26]=[CH2:27])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 59924653HCID 59924653, compound

Product 1

HCID 59924954HCID 59924954, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared from 44 mg of 2-[(S)-1-phenylethylamino]-4-[5-iodobenzimidazol-1-yl]pyrimidine, 87 μL tributylstannyl ethylene and 1.15 mg Pd(PPh3)4 using the procedure described in EXAMPLE 273 to give 8.5 mg of the title compound. RF: 0.45 (5% MeOH in CH2Cl2). 1H NMR (500 MHz, 1:1 CD3OD/CDCl3): δ 1.59 (d, J=6.8 Hz, 3H), 5.13 (m, 1H), 5.24 (d, J=11.2 Hz, 1H), 5.76 (d, J=17.4 Hz, 1H), 6.79 (dd, J=17.6, 11 Hz, 1H), 6.87 (d, J=5.7 Hz, 1H), 7.21 (br s, J=7.3 Hz, 1H), 7.27-7.34 (m, 3H), 7.41 (br s, J=7.3 Hz, 2H), 7.6-7.8 (m, 1H), 7.67 (br s, 1H), 8.31 (br s, J=5.7 Hz, 1H), 8.55-8.7 (m, 1H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 342.3 (M+1).

Sources & evidence

ORD record
ord-57ca2483eb28464b96f7feb024663501
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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