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

HRID 1642421Notes

Reaction equation

HRID 1642421 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:19][CH:18]=[CH:17][N:5]2[C:6](=[O:16])[C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[CH3:20][O:21][C:22]1[C:23]([O:30][CH2:31][CH2:32][O:33][CH3:34])=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.[O-]CC.[Na+]>>[CH3:20][O:21][C:22]1[C:23]([O:30][CH2:31][CH2:32][O:33][CH3:34])=[C:24](/[CH:25]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:19][CH:18]=[CH:17][N:5]3[C:6](=[O:16])[C:7]=2[C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 2723922Sodium ethoxideHCID 230098862-(2-Methoxyethoxy)-3-methoxybenzaldehydeHCID 66752927HCID 66752927, compound

Product 1

HCID 444680814-{7-[(E)-2-(3-Methoxy-2-(2-methoxyethoxy)phenyl]-1-ethenyl}-5-oxo-5H-[1,3]-thiazolo[3,2-a]pyrimidin-6-yl}benzonitrileYield 40.3%

Procedure

The title compound was prepared by condensation of Intermediate 4 (350 mg, 1.312 mmol) with 3-methoxy-2-(2-methoxyethoxy)benzaldehyde (385 mg, 1.833 mmol) in presence of sodium ethoxide (178 mg, 2.624 mmol) according to the procedure outlined in Example 9 to afford 243 mg of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.47-3.53 (m, 2H), 3.70 (s, 3H), 3.78 (s, 3H), 3.99-4.05 (m, 2H), 6.79 (d, J=15.6 Hz, 1H), 6.93-7.01 (m, 3H), 7.50-7.58 (m, 3H), 7.92 (d, J=8.1 Hz, 2H), 8.01 (d, J=4.8 Hz, 1H), 8.22 (d, J=15.9 Hz, 1H); ESI-MS (m/z) 460.50 (M+H)+.

Sources & evidence

ORD record
ord-bcc698d4b9ee45b2a395159735c86fa7
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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