Ethanol → 6-(4-Dimethylaminophenyl)-7-[(E)-2-(2-isobutoxy-3-methoxyphenyl)-1-ethenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
Reaction equation
I[C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][S:11][C:5]2=[N:4][C:3]=1/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=1[O:22][CH2:23][CH:24]([CH3:26])[CH3:25].C(=O)([O-])[O-].[Na+].[Na+].[CH2:33](O)[CH3:34].O>C1(C)C=CC=CC=1>[CH3:3][N:4]([CH3:5])[C:34]1[CH:33]=[CH:15][C:14]([C:2]2[C:7](=[O:8])[N:6]3[CH:9]=[CH:10][S:11][C:5]3=[N:4][C:3]=2/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=2[O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:13][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared from Intermediate 7 (100 mg, 0.207 mmol), 4-N,N-dimethylaminophenylboronic acid (47 mg, 0.290 mmol), Pd[(C6H5)3P]4 (10 mg, 0.009 mmol) and sodium carbonate (131 mg, 1.244 mmol) in a mixture of toluene, ethanol and water according to the procedure outlined in Example 1 to afford a crude product which was purified by silica gel column chromatography using 10% ethyl acetate in chloroform to give 75 mg of the product; 1H NMR (300 MHz, DMSO-d6) δ 0.98 (d, J=6.9 Hz, 6H), 1.85-1.89 (m, 1H), 2.95 (s, 6H), 3.62 (d, J=6.3 Hz, 2H), 3.77 (s, 3H), 6.77 (d, J=9.0 Hz, 2H), 6.82-6.92 (m, 1H), 6.98-7.04 (m, 3H), 7.15 (d, J=9.0 Hz, 1H), 7.45 (d, J=4.8 Hz, 1H), 7.95 (d, J=4.8 Hz, 1H), 8.08 (d, J=15.6 Hz, 1H); ESI-MS (m/z) 476.46 (M+H)+.
Workup
- customto afford a crude product which
Sources & evidence
- ORD record
- ord-4de07006fcd24fff8cf50916d8270f54
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119647B2
Reaction notes
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