Sodium ethoxide → 7-[(E)-2-{3-Methoxy-2-(2-methoxyethoxy)phenyl}-1-ethenyl]-6-[4-(trifluoro methoxy)-phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642453Notes

Reaction equation

HRID 1642453 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][O:36][CH3:37])=[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][O:36][CH3:37])=[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 230098862-(2-Methoxyethoxy)-3-methoxybenzaldehydeHCID 66753265HCID 66753265, compound

Product 1

HCID 444678127-[(E)-2-{3-Methoxy-2-(2-methoxyethoxy)phenyl}-1-ethenyl]-6-[4-(trifluoro methoxy)-phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 51.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by condensation of Intermediate 15 (350 mg, 1.072 mmol) with 3-methoxy-2-(2-methoxyethoxy)benzaldehyde (316 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 286 mg of the desired product as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 3.33-3.40 (m, 3H), 3.45-3.51 (m, 2H), 3.78 (s, 3H), 3.95-4.03 (m, 2H), 6.82 (d, J=15.6 Hz, 1H), 6.85-6.91 (m, 1H), 7.00 (d, J=4.2 Hz, 2H), 7.45-7.52 (m, 5H), 8.00 (d, J=4.8 Hz, 1H), 8.19 (d, J=15.6 Hz, 1H); ESI-MS (m/z) 518.19 (M+H)+.

Sources & evidence

ORD record
ord-9376d291213d43d4b7c38236c66b90c8
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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