Dimethylformamide → HCID 9952707, compound

HRID 2300813Notes

Reaction equation

HRID 2300813 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.C([Sn](CCCC)(CCCC)[C:31]1[S:32][CH:33]=C[CH:35]=1)CCC.C[N:45](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.C(OCC)C>[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]([C:33]5[S:32][CH:31]=[CH:35][N:45]=5)=[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

6

Reactant 3

HCID 6228DimethylformamideHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 59924653HCID 59924653, compound

Product 1

HCID 9952707HCID 9952707, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A solution containing 28 mg of 2-[(S)-1-phenylethylamino]-4-[5-iodobenzimidazol-1-yl]pyrimidine, 60 μL 2-(tributylstannyl)-thiophene, 0.7 mg Pd(PPh3)4 and 3 mL DMF was stirred under nitrogen at 100° C. for 2 hours. The solution was cooled to room temperature, added to 100 mL of ethyl ether, washed three times with water and then once with brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with methanol in methylene chloride to give 11.1 mg of the title compound. RF: 0.5 (5% MeOH in CH2Cl2). 1H NMR (500 MHz, CD3OD): δ 1.59 (d, J=7.1 Hz, 3H), 5.13 (m, 1H), 6.90 (d, J=5.7 Hz, 1H), 7.06 (dd, J=5.0, 3.7 Hz, 1H), 7.22 (t, J=7.3 Hz, 1H), 7.29-7.54 (m, 7H), 7.76 (m, 1H), 7.86 (br s, 1H), 8.31 (br s, J=5.2 Hz, 1H), 8.68 (m, 1H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 398.1 (M+1).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. washwashed three times with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with methanol in methylene chloride

Sources & evidence

ORD record
ord-7ae5a0a5c20f4c868c7e6bfa908e3ec7
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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