Sodium ethoxide → 7-[(E)-2-(3-Methoxy-2-pentyloxyphenyl)-1-ethenyl]-6-[4-(trifluoromethoxy)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642447Notes

Reaction equation

HRID 1642447 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:22][CH:21]=[CH:20][N:5]2[C:6](=[O:19])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.[CH3:23][O:24][C:25]1[C:26]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=O.[O-]CC.[Na+]>C(O)C>[CH3:23][O:24][C:25]1[C:26]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[C:27](/[CH:28]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:22][CH:21]=[CH:20][N:5]3[C:6](=[O:19])[C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:17])([F:18])[F:16])=[CH:10][CH:9]=2)[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 193632903-Methoxy-2-(pentyloxy)benzaldehydeHCID 66753265HCID 66753265, compound

Product 1

HCID 444676007-[(E)-2-(3-Methoxy-2-pentyloxyphenyl)-1-ethenyl]-6-[4-(trifluoromethoxy)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 45.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by condensation of Intermediate 15 (350 mg, 1.071 mmol) with 3-methoxy-2-pentyloxybenzaldehyde (333 mg, 1.501 mmol) in presence of sodium ethoxide (146 mg, 2.147 mmol) in ethanol (15 ml) according to the procedure of Example 24 to give 261 mg of the desired product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.91 (t, J=6.6 Hz, 3H), 1.33-1.42 (m, 4H), 1.50-1.58 (m, 2H), 3.77 (s, 3H), 3.83 (t, J=6.3 Hz, 2H), 6.85-6.90 (m, 2H), 6.96-7.02 (m, 2H), 7.40-7.47 (m, 4H), 7.51-7.90 (m, 1H), 7.95-8.02 (m, 1H), 8.06-8.12 (m, 1H); ESI-MS (m/z) 531.26 (M+H)+.

Sources & evidence

ORD record
ord-d098dea386db47e795a571bb651f7ac1
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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