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

HRID 1642426Notes

Reaction equation

HRID 1642426 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:21][CH:20]=[CH:19][N:5]2[C:6](=[O:18])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[CH3:22][O:23][C:24]1[C:25]([O:32][CH2:33][CH2:34][CH3:35])=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O.[O-]CC.[Na+]>C(O)C>[CH3:22][O:23][C:24]1[C:25]([O:32][CH2:33][CH2:34][CH3:35])=[C:26](/[CH:27]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:21][CH:20]=[CH:19][N:5]3[C:6](=[O:18])[C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=2)[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 31593253-Methoxy-2-propoxybenzaldehydeHCID 667528027-Methyl-6-[4-(trifluoromethyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 444671587-[(E)-2-(3-Methoxy-2-propoxyphenyl)-1-ethenyl]-6-[4-(trifluoromethyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by condensation of Intermediate 5 (400 mg, 1.289 mmol) with 3-methoxy-2-propoxybenzaldehyde (375 mg, 1.933 mmol) in presence of sodium ethoxide (175 mg, 2.578 mmol) in ethanol (15 ml) according to the procedure described in Example 24 to give 310 mg of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.93 (t, J=6.6 Hz, 3H), 1.48 (q, J=6.9 Hz, 2H), 3.77 (s, 5H), 6.93-7.00 (m, 4H), 7.52-7.59 (m, 3H), 7.82 (d, J=7.8 Hz, 2H), 7.98-8.02 (m, 2H); ESI-MS (m/z) 487.35 (M+H)+.

Sources & evidence

ORD record
ord-0dca811dd3ac447e8028a20c7e02d5b6
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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